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id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-Abbreviations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Abbreviations"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Abbreviations</span> </div> </a> <ul id="toc-Abbreviations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactivity_of_benzylic_centers" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactivity_of_benzylic_centers"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reactivity of benzylic centers</span> </div> </a> <button aria-controls="toc-Reactivity_of_benzylic_centers-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactivity of benzylic centers subsection</span> </button> <ul id="toc-Reactivity_of_benzylic_centers-sublist" class="vector-toc-list"> <li id="toc-Functionalization_at_the_benzylic_position" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Functionalization_at_the_benzylic_position"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Functionalization at the benzylic position</span> </div> </a> <ul id="toc-Functionalization_at_the_benzylic_position-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-As_a_protecting_group" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#As_a_protecting_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>As a protecting group</span> </div> </a> <button aria-controls="toc-As_a_protecting_group-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle As a protecting group subsection</span> </button> <ul id="toc-As_a_protecting_group-sublist" class="vector-toc-list"> <li id="toc-Alcohol_protection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alcohol_protection"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Alcohol protection</span> </div> </a> <ul id="toc-Alcohol_protection-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deprotection_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Deprotection_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Deprotection methods</span> </div> </a> <ul id="toc-Deprotection_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-The_p-methoxybenzyl_protecting_group" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#The_p-methoxybenzyl_protecting_group"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>The <i>p</i>-methoxybenzyl protecting group</span> </div> </a> <ul id="toc-The_p-methoxybenzyl_protecting_group-sublist" class="vector-toc-list"> <li id="toc-Deprotection_methods_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Deprotection_methods_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.1</span> <span>Deprotection methods</span> </div> </a> <ul id="toc-Deprotection_methods_2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Amine_protection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Amine_protection"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Amine protection</span> </div> </a> <ul id="toc-Amine_protection-sublist" class="vector-toc-list"> <li id="toc-Deprotection_methods_3" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Deprotection_methods_3"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4.1</span> <span>Deprotection methods</span> </div> </a> <ul id="toc-Deprotection_methods_3-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Benzyl group</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 30 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-30" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%AC%D9%85%D9%88%D8%B9%D8%A9_%D8%A8%D9%86%D8%B2%D9%8A%D9%84" title="مجموعة بنزيل – Arabic" lang="ar" hreflang="ar" data-title="مجموعة بنزيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Benzil_grupa" title="Benzil grupa – Bosnian" lang="bs" hreflang="bs" data-title="Benzil grupa" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Benzyl" title="Benzyl – Czech" lang="cs" hreflang="cs" data-title="Benzyl" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Bensyl" title="Bensyl – Welsh" lang="cy" hreflang="cy" data-title="Bensyl" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Benzyl" title="Benzyl – Danish" lang="da" hreflang="da" data-title="Benzyl" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Benzylgruppe" title="Benzylgruppe – German" lang="de" hreflang="de" data-title="Benzylgruppe" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Bens%C3%BC%C3%BClr%C3%BChm" title="Bensüülrühm – Estonian" lang="et" hreflang="et" data-title="Bensüülrühm" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Bencilo" title="Bencilo – Spanish" lang="es" hreflang="es" data-title="Bencilo" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Bentzilo_talde" title="Bentzilo talde – Basque" lang="eu" hreflang="eu" data-title="Bentzilo talde" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D8%B1%D9%88%D9%87_%D8%A8%D9%86%D8%B2%DB%8C%D9%84" title="گروه بنزیل – Persian" lang="fa" hreflang="fa" data-title="گروه بنزیل" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Benzyle" title="Benzyle – French" lang="fr" hreflang="fr" data-title="Benzyle" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Beinsil" title="Beinsil – Irish" lang="ga" hreflang="ga" data-title="Beinsil" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B2%A4%EC%A7%88%EA%B8%B0" title="벤질기 – Korean" lang="ko" hreflang="ko" data-title="벤질기" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Benzile" title="Benzile – Italian" lang="it" hreflang="it" data-title="Benzile" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%91%D7%A0%D7%96%D7%99%D7%9C" title="בנזיל – Hebrew" lang="he" hreflang="he" data-title="בנזיל" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Benzilcsoport" title="Benzilcsoport – Hungarian" lang="hu" hreflang="hu" data-title="Benzilcsoport" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Benzylgroep" title="Benzylgroep – Dutch" lang="nl" hreflang="nl" data-title="Benzylgroep" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%99%E3%83%B3%E3%82%B8%E3%83%AB%E5%9F%BA" title="ベンジル基 – Japanese" lang="ja" hreflang="ja" data-title="ベンジル基" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%AC%E0%A9%88%E0%A8%A8%E0%A8%9C%E0%A8%BC%E0%A8%BE%E0%A8%88%E0%A8%B2" title="ਬੈਨਜ਼ਾਈਲ – Punjabi" lang="pa" hreflang="pa" data-title="ਬੈਨਜ਼ਾਈਲ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Grupa_benzylowa" title="Grupa benzylowa – Polish" lang="pl" hreflang="pl" data-title="Grupa benzylowa" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Benzil" title="Benzil – Portuguese" lang="pt" hreflang="pt" data-title="Benzil" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Benzil" title="Benzil – Romanian" lang="ro" hreflang="ro" data-title="Benzil" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%B3%D1%80%D1%83%D0%BF%D0%BF%D0%B0" title="Бензильная группа – Russian" lang="ru" hreflang="ru" data-title="Бензильная группа" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Benzil_grupa" title="Benzil grupa – Serbian" lang="sr" hreflang="sr" data-title="Benzil grupa" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Benzil_grupa" title="Benzil grupa – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Benzil grupa" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Bentsyyli" title="Bentsyyli – Finnish" lang="fi" hreflang="fi" data-title="Bentsyyli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Bensylgrupp" title="Bensylgrupp – Swedish" lang="sv" hreflang="sv" data-title="Bensylgrupp" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%86%E0%AE%A9%E0%AF%8D%E0%AE%9A%E0%AF%88%E0%AE%B2%E0%AF%8D" title="பென்சைல் – Tamil" lang="ta" hreflang="ta" data-title="பென்சைல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8B%84%E5%9F%BA" title="苄基 – Wu" lang="wuu" hreflang="wuu" data-title="苄基" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%84%E5%9F%BA" title="苄基 – Chinese" lang="zh" hreflang="zh" data-title="苄基" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q818534#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div 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<style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Benzil" title="Benzil">benzil</a>, <a href="/wiki/Benzoyl" class="mw-redirect" title="Benzoyl">benzoyl</a>, or <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a>.</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Benzyl_group_V.9.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Benzyl_group_V.9.svg/500px-Benzyl_group_V.9.svg.png" decoding="async" width="500" height="323" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Benzyl_group_V.9.svg/750px-Benzyl_group_V.9.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Benzyl_group_V.9.svg/1000px-Benzyl_group_V.9.svg.png 2x" data-file-width="514" data-file-height="332" /></a><figcaption><style data-mw-deduplicate="TemplateStyles:r1239334494">@media screen{html.skin-theme-clientpref-night .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}</style><span class="tmp-color" style="color:blue">Benzyl group and derivatives</span>: Benzyl group, benzyl <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a>, <a href="/wiki/Benzyl_amine" class="mw-redirect" title="Benzyl amine">benzyl amine</a>, <a href="/wiki/Benzyl_bromide" title="Benzyl bromide">benzyl bromide</a>, <a href="/wiki/Benzyl_chloroformate" title="Benzyl chloroformate">benzyl chloroformate</a>, and benzyl methyl ether. R = heteroatom, <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a>, <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>, <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a> etc. or other substituents.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>benzyl</b> is the <a href="/wiki/Substituent" title="Substituent">substituent</a> or molecular fragment possessing the structure <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R−CH<sub class="template-chem2-sub">2</sub>−C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub></span>. Benzyl features a <a href="/wiki/Benzene" title="Benzene">benzene</a> ring (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub></span>) attached to a <a href="/wiki/Methylene_group" title="Methylene group">methylene group</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>−</span>).<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC nomenclature</a>, the prefix <b>benzyl</b> refers to a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">2</sub></span> substituent, for example <a href="/wiki/Benzyl_chloride" title="Benzyl chloride">benzyl chloride</a> or <a href="/wiki/Benzyl_benzoate" title="Benzyl benzoate">benzyl benzoate</a>. Benzyl is not to be confused with <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub></span>. The term <b>benzylic</b> is used to describe the position of the first carbon bonded to a benzene or other <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> ring. For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C<sup class="template-chem2-sup">+</sup></span> is referred to as a "benzylic" carbocation. The benzyl <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radical</a> has the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">2</sub>•</span>. The benzyl cation or phenylcarbenium ion is the <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> with formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span>; the benzyl anion or phenylmethanide ion is the <a href="/wiki/Carbanion" title="Carbanion">carbanion</a> with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<span class="template-chem2-su"><span>−</span><span>2</span></span></span>. None of these species can be formed in significant amounts in the solution phase under normal conditions, but they are useful referents for discussion of <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">reaction mechanisms</a> and may exist as reactive intermediates. </p> <div class="mw-heading mw-heading3"><h3 id="Abbreviations">Abbreviations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=2" title="Edit section: Abbreviations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzyl is most commonly abbreviated Bn. For example, <a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">benzyl alcohol</a> can be represented as BnOH. Less common abbreviations are Bzl and Bz, the latter of which is ambiguous as it is also the standard abbreviation for the <a href="/wiki/Benzoyl" class="mw-redirect" title="Benzoyl">benzoyl</a> group <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>C(O)−</span>. Likewise, benzyl should not be confused with the phenyl group <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>−</span>, abbreviated Ph. </p> <div class="mw-heading mw-heading2"><h2 id="Reactivity_of_benzylic_centers">Reactivity of benzylic centers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=3" title="Edit section: Reactivity of benzylic centers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The enhanced reactivity of benzylic positions is attributed to the low <a href="/wiki/Bond_dissociation_energy" class="mw-redirect" title="Bond dissociation energy">bond dissociation energy</a> for benzylic C−H bonds. Specifically, the bond <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">2</sub>−H</span> is about 10–15% weaker than other kinds of C−H bonds. The neighboring aromatic ring stabilizes benzyl radicals. The data tabulated below compare benzylic C−H bond to related C−H bond strengths. </p> <table class="wikitable" style="text-align:center"> <tbody><tr> <th rowspan="2">Bond </th> <th rowspan="2">Bond </th> <th colspan="2">Bond-dissociation energy<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bord_3-0" class="reference"><a href="#cite_note-Bord-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </th> <th rowspan="2">Comment </th></tr> <tr> <th>(kcal/mol) </th> <th>(kJ/mol) </th></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">2</sub>−H</span> </td> <td>benzylic C−H bond </td> <td>90 </td> <td>377 </td> <td>akin to allylic C−H bonds<br />such bonds show enhanced reactivity </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C−H</span> </td> <td><a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> C−H bond </td> <td>105 </td> <td>439 </td> <td>one of the strongest aliphatic C−H bonds </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">5</sub>−H</span> </td> <td><a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> C−H bond </td> <td>101 </td> <td>423 </td> <td>slightly weaker than <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C−H</span> </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>−H</span> </td> <td><a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> C−H bond </td> <td>113 </td> <td>473 </td> <td>comparable to vinyl radical, rare </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHCH<sub class="template-chem2-sub">2</sub>−H</span> </td> <td><a href="/wiki/Allylic" class="mw-redirect" title="Allylic">allylic</a> C–H bond </td> <td>89 </td> <td>372 </td> <td>similar to benzylic C-H </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>)<sub class="template-chem2-sub">2</sub>CH−H</span> </td> <td><a href="/wiki/Fluorenyl" class="mw-redirect" title="Fluorenyl">fluorenyl</a> C–H bond </td> <td>80 </td> <td> </td> <td>more activated vs diphenylmethyle (<a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> = 22.6) </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>CH−H</span> </td> <td><a href="/wiki/Benzhydryl_compounds" title="Benzhydryl compounds">diphenylmethyl</a> C–H bond </td> <td>82 </td> <td> </td> <td>"doubly benzylic" (<a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> = 32.2) </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">3</sub>C−H</span> </td> <td><a href="/wiki/Trityl" class="mw-redirect" title="Trityl">trityl</a> C–H bond </td> <td>81 </td> <td>339 </td> <td>"triply benzylic" </td></tr> </tbody></table> <p>The weakness of the C−H bond reflects the stability of the benzylic radical. For related reasons, benzylic substituents exhibit enhanced reactivity, as in <a href="/wiki/KMnO4#Organic_chemistry" class="mw-redirect" title="KMnO4">oxidation</a>, <a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">free radical halogenation</a>, or <a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">hydrogenolysis</a>. As a practical example, in the presence of suitable catalysts, <i>p</i>-<a href="/wiki/Xylene" title="Xylene">xylene</a> oxidizes exclusively at the benzylic positions to give <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {CH3C6H4CH3 + 3 O2 -> HO2CC6H4CO2H + 2 H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>3</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>H</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {CH3C6H4CH3 + 3 O2 -> HO2CC6H4CO2H + 2 H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/686d432cc861a6b50cf0fefec8577d00c925bfda" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:53.921ex; height:2.843ex;" alt="{\displaystyle {\ce {CH3C6H4CH3 + 3 O2 -> HO2CC6H4CO2H + 2 H2O}}}"></span></dd></dl> <p>Millions of tonnes of terephthalic acid are produced annually by this method.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Functionalization_at_the_benzylic_position">Functionalization at the benzylic position</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=4" title="Edit section: Functionalization at the benzylic position"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a few cases, these benzylic transformations occur under conditions suitable for lab synthesis. The <a href="/wiki/Wohl%E2%80%93Ziegler_bromination" title="Wohl–Ziegler bromination">Wohl-Ziegler reaction</a> will brominate a benzylic C–H bond: (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ArCHR<sub class="template-chem2-sub">2</sub> → ArCBrR<sub class="template-chem2-sub">2</sub></span>).<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Any non-tertiary benzylic alkyl group will be oxidized to a carboxyl group by aqueous potassium permanganate (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KMnO<sub class="template-chem2-sub">4</sub></span>) or concentrated nitric acid (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HNO<sub class="template-chem2-sub">3</sub></span>): (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ArCHR<sub class="template-chem2-sub">2</sub> → ArCOOH</span>).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Finally, the complex of <a href="/wiki/Chromium_trioxide" title="Chromium trioxide">chromium trioxide</a> and <a href="/wiki/3,5-Dimethylpyrazole" title="3,5-Dimethylpyrazole">3,5-dimethylpyrazole</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CrO<sub class="template-chem2-sub">3</sub>−dmpyz</span>) will selectively oxidize a benzylic methylene group to a carbonyl: (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ArCH<sub class="template-chem2-sub">2</sub>R → ArC(O)R</span>).<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/2-Iodoxybenzoic_acid" title="2-Iodoxybenzoic acid">2-iodoxybenzoic acid</a> in DMSO performs similarly.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="As_a_protecting_group">As a protecting group</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=5" title="Edit section: As a protecting group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzyl groups are occasionally employed as protecting groups in organic synthesis. Their installation and especially their removal require relatively harsh conditions, so benzyl is not typically preferred for protection.<sup id="cite_ref-:0_9-0" class="reference"><a href="#cite_note-:0-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Alcohol_protection">Alcohol protection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=6" title="Edit section: Alcohol protection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzyl is commonly used in organic synthesis as a robust protecting group for <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> and <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>. </p> <ul><li>Treatment of alcohol with a strong base such as powdered <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a> or <a href="/wiki/Sodium_hydride" title="Sodium hydride">sodium hydride</a> and benzyl halide (<a href="/wiki/Benzyl_chloride" title="Benzyl chloride">BnCl</a> or <a href="/wiki/Benzyl_bromide" title="Benzyl bromide">BnBr</a>)<sup id="cite_ref-:0_9-1" class="reference"><a href="#cite_note-:0-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:BnProtectedalcohol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/BnProtectedalcohol.png/455px-BnProtectedalcohol.png" decoding="async" width="455" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/BnProtectedalcohol.png/683px-BnProtectedalcohol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/BnProtectedalcohol.png/910px-BnProtectedalcohol.png 2x" data-file-width="1411" data-file-height="344" /></a><figcaption></figcaption></figure></dd></dl></li> <li>Monobenzylation of <a href="/wiki/Diol" title="Diol">diols</a> can be achieved using <a href="/wiki/Silver(I)_oxide" class="mw-redirect" title="Silver(I) oxide">Ag<sub>2</sub>O</a> in <a href="/wiki/Dimethylformamide" title="Dimethylformamide">dimethylformamide</a> (DMF) at ambient to elevated temperatures<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Primary_alcohol" title="Primary alcohol">Primary alcohols</a> can be selectively benzylated in presence of phenol functional groups using <a href="/wiki/Metal_acetylacetonates" title="Metal acetylacetonates">Cu(acac)<sub>2</sub></a><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Deprotection_methods">Deprotection methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=7" title="Edit section: Deprotection methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzyl ethers can be removed under <i><a href="/wiki/Redox" title="Redox">reductive</a> conditions</i>, <i><a href="/wiki/Oxidative" class="mw-redirect" title="Oxidative">oxidative</a> conditions</i>, and the use of <i>Lewis acids</i>.<sup id="cite_ref-:0_9-2" class="reference"><a href="#cite_note-:0-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Removed using <a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">hydrogenolysis</a><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:BnEtherExample.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/BnEtherExample.png/626px-BnEtherExample.png" decoding="async" width="626" height="209" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/BnEtherExample.png/939px-BnEtherExample.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/BnEtherExample.png/1252px-BnEtherExample.png 2x" data-file-width="1928" data-file-height="643" /></a><figcaption></figcaption></figure></dd></dl></li> <li>Single electron process with <a href="/wiki/Sodium" title="Sodium">Na</a>/<a href="/wiki/Ammonia" title="Ammonia">NH<sub>3</sub></a> or <a href="/wiki/Lithium" title="Lithium">Li</a>/NH<sub>3</sub></li></ul> <ul><li>Benzyl protecting groups can be removed using a wide range of oxidizing agents including: <ul><li><a href="/wiki/Chromium_trioxide" title="Chromium trioxide">CrO<sub>3</sub></a>/<a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> at ambient temperature</li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/N-Bromosuccinimide" title="N-Bromosuccinimide"><i>N</i>-Bromosuccinimide</a> (NBS)</li> <li><a href="/wiki/N-Iodosuccinimide" title="N-Iodosuccinimide"><i>N</i>-Iodosuccinimide</a> (NIS)</li></ul></li></ul> <ul><li><a href="/wiki/Trimethylsilyl" class="mw-redirect" title="Trimethylsilyl">Trimethylsilyl</a> iodide (Me<sub>3</sub>SiI) in <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a> at ambient temperature (selectivity can be achieved under specific conditions)</li></ul> <div class="mw-heading mw-heading3"><h3 id="The_p-methoxybenzyl_protecting_group">The <i>p</i>-methoxybenzyl protecting group</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=8" title="Edit section: The p-methoxybenzyl protecting group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>p</i>-Methoxybenzyl (<b>PMB</b>) is used as a <a href="/wiki/Protecting_group" title="Protecting group">protecting group</a> for <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a> in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> (<a href="/wiki/4-Methoxybenzylthiol" title="4-Methoxybenzylthiol">4-Methoxybenzylthiol</a> is used to protect thiols). </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:PMB_Ether.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/PMB_Ether.png/220px-PMB_Ether.png" decoding="async" width="220" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/PMB_Ether.png/330px-PMB_Ether.png 1.5x, //upload.wikimedia.org/wikipedia/commons/d/d6/PMB_Ether.png 2x" data-file-width="421" data-file-height="177" /></a><figcaption>The <i>p</i>-methoxybenzyl group</figcaption></figure> <ul><li>Strong base such as powdered <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a> or <a href="/wiki/Sodium_hydride" title="Sodium hydride">sodium hydride</a> and <i>p</i>-methoxybenzyl halide (chloride or bromide)<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li>4-methoxybenzyl-2,2,2-trichloroacetimidate can be used to install the PMB group in presence of: <ul><li><a href="/wiki/Scandium(III)_trifluoromethanesulfonate" title="Scandium(III) trifluoromethanesulfonate">Scandium (III) triflate</a> (Sc(OTf)<sub>3</sub>) in toluene at 0 °C<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Trifluoromethanesulfonic_acid" class="mw-redirect" title="Trifluoromethanesulfonic acid">Trifluoromethanesulfonic acid</a> (TfOH) in <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a> at 0 °C<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:PMBAlcohol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/PMBAlcohol.png/676px-PMBAlcohol.png" decoding="async" width="676" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/PMBAlcohol.png/1014px-PMBAlcohol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/PMBAlcohol.png/1352px-PMBAlcohol.png 2x" data-file-width="2042" data-file-height="333" /></a><figcaption></figcaption></figure></dd></dl></li></ul></li></ul> <div class="mw-heading mw-heading4"><h4 id="Deprotection_methods_2">Deprotection methods</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=9" title="Edit section: Deprotection methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>2,3-Dichloro-5,6-dicyano-<i>p</i>-benzoquinone (DDQ)<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:PMBDeprotection.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/PMBDeprotection.png/674px-PMBDeprotection.png" decoding="async" width="674" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/PMBDeprotection.png/1011px-PMBDeprotection.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/PMBDeprotection.png/1348px-PMBDeprotection.png 2x" data-file-width="2105" data-file-height="365" /></a><figcaption></figcaption></figure></dd></dl></li> <li>Conditions for deprotection of benzyl group are applicable for cleavage of the PMB protecting group</li></ul> <div class="mw-heading mw-heading3"><h3 id="Amine_protection">Amine protection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=10" title="Edit section: Amine protection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The benzyl group is occasionally used as a <a href="/wiki/Protecting_group" title="Protecting group">protecting group</a> for <a href="/wiki/Amine" title="Amine">amines</a> in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. Other methods exist.<sup id="cite_ref-:0_9-3" class="reference"><a href="#cite_note-:0-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Aqueous <a href="/wiki/Potassium_carbonate" title="Potassium carbonate">potassium carbonate</a> and benzyl halide (<a href="/wiki/Benzyl_chloride" title="Benzyl chloride">BnCl</a>, <a href="/wiki/Benzyl_bromide" title="Benzyl bromide">BnBr</a>) in <a href="/wiki/Methanol" title="Methanol">methanol</a><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:Bn_protection_with_bnbr.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Bn_protection_with_bnbr.png/609px-Bn_protection_with_bnbr.png" decoding="async" width="609" height="141" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Bn_protection_with_bnbr.png/914px-Bn_protection_with_bnbr.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Bn_protection_with_bnbr.png/1218px-Bn_protection_with_bnbr.png 2x" data-file-width="1608" data-file-height="373" /></a><figcaption></figcaption></figure></dd></dl></li> <li><a href="/wiki/Benzaldehyde" title="Benzaldehyde">Benzaldehyde</a>, 6 M <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a> and <a href="/wiki/Sodium_cyanoborohydride" title="Sodium cyanoborohydride">NaBH<sub>3</sub>CN</a> in <a href="/wiki/Methanol" title="Methanol">methanol</a><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> <dl><dd><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:Bn_protection_with_benzaldehyde.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Bn_protection_with_benzaldehyde.png/532px-Bn_protection_with_benzaldehyde.png" decoding="async" width="532" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Bn_protection_with_benzaldehyde.png/798px-Bn_protection_with_benzaldehyde.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Bn_protection_with_benzaldehyde.png/1064px-Bn_protection_with_benzaldehyde.png 2x" data-file-width="1161" data-file-height="261" /></a><figcaption></figcaption></figure></dd></dl></li></ul> <div class="mw-heading mw-heading4"><h4 id="Deprotection_methods_3">Deprotection methods</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=11" title="Edit section: Deprotection methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a> in the presence of the <a href="/wiki/Palladium" title="Palladium">palladium</a> catalyst<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></li></ul> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:QIGLEZ.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/QIGLEZ.svg/220px-QIGLEZ.svg.png" decoding="async" width="220" height="226" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/QIGLEZ.svg/330px-QIGLEZ.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f2/QIGLEZ.svg/440px-QIGLEZ.svg.png 2x" data-file-width="1200" data-file-height="1234" /></a><figcaption>Structure of <a href="/wiki/Tetrabenzylzirconium" title="Tetrabenzylzirconium">tetrabenzylzirconium</a> with H atoms omitted for clarity.<sup id="cite_ref-Parkin_22-0" class="reference"><a href="#cite_note-Parkin-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Benzylamine" title="Benzylamine">Benzylamine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzyl_group&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFCareySundberg2008" class="citation book cs1">Carey, F. A.; Sundberg, R. J. (2008). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/advancedorganicc00care_636"><i>Advanced Organic Chemistry, Part A: Structure and Mechanisms</i></a></span> (5th ed.). New York, NY: Springer. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/advancedorganicc00care_636/page/n829">806</a>–808, <span class="nowrap">312–</span>313. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780387448978" title="Special:BookSources/9780387448978"><bdi>9780387448978</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%2C+Part+A%3A+Structure+and+Mechanisms&rft.place=New+York%2C+NY&rft.pages=806-808%2C+%3Cspan+class%3D%22nowrap%22%3E312-%3C%2Fspan%3E313&rft.edition=5th&rft.pub=Springer&rft.date=2008&rft.isbn=9780387448978&rft.aulast=Carey&rft.aufirst=F.+A.&rft.au=Sundberg%2C+R.+J.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fadvancedorganicc00care_636&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFXueJiZhouCheng2017" class="citation journal cs1">Xue, Xiao-Song; Ji, Pengju; Zhou, Biying; Cheng, Jin-Pei (2017). "The Essential Role of Bond Energetics in C–H Activation/Functionalization". <i>Chemical Reviews</i>. <b>117</b> (13): <span class="nowrap">8622–</span>8648. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.chemrev.6b00664">10.1021/acs.chemrev.6b00664</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28281752">28281752</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=The+Essential+Role+of+Bond+Energetics+in+C%E2%80%93H+Activation%2FFunctionalization&rft.volume=117&rft.issue=13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8622-%3C%2Fspan%3E8648&rft.date=2017&rft_id=info%3Adoi%2F10.1021%2Facs.chemrev.6b00664&rft_id=info%3Apmid%2F28281752&rft.aulast=Xue&rft.aufirst=Xiao-Song&rft.au=Ji%2C+Pengju&rft.au=Zhou%2C+Biying&rft.au=Cheng%2C+Jin-Pei&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-Bord-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bord_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangBordwell1992" class="citation journal cs1">Zhang, Xian-Man; Bordwell, Frederick G. (1992). "Homolytic bond dissociation energies of the benzylic carbon-hydrogen bonds in radical anions and radical cations derived from fluorenes, triphenylmethanes, and related compounds". <i>Journal of the American Chemical Society</i>. <b>114</b> (25): <span class="nowrap">9787–</span>9792. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00051a010">10.1021/ja00051a010</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Homolytic+bond+dissociation+energies+of+the+benzylic+carbon-hydrogen+bonds+in+radical+anions+and+radical+cations+derived+from+fluorenes%2C+triphenylmethanes%2C+and+related+compounds&rft.volume=114&rft.issue=25&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9787-%3C%2Fspan%3E9792&rft.date=1992&rft_id=info%3Adoi%2F10.1021%2Fja00051a010&rft.aulast=Zhang&rft.aufirst=Xian-Man&rft.au=Bordwell%2C+Frederick+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSheehan" class="citation encyclopaedia cs1">Sheehan, Richard J. "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a26_193">10.1002/14356007.a26_193</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Terephthalic+Acid%2C+Dimethyl+Terephthalate%2C+and+Isophthalic+Acid&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a26_193&rft.isbn=978-3-527-30673-2&rft.aulast=Sheehan&rft.aufirst=Richard+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFC.2018" class="citation book cs1">C., Vollhardt, K. Peter (2018-01-29). <i>Organic chemistry : structure and function</i>. Schore, Neil Eric, 1948- (8e ed.). New York. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781319079451" title="Special:BookSources/9781319079451"><bdi>9781319079451</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1007924903">1007924903</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry+%3A+structure+and+function&rft.place=New+York&rft.edition=8e&rft.date=2018-01-29&rft_id=info%3Aoclcnum%2F1007924903&rft.isbn=9781319079451&rft.aulast=C.&rft.aufirst=Vollhardt%2C+K.+Peter&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>) CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChandler)1993" class="citation book cs1">Chandler), Norman, R. O. C. (Richard Oswald (1993). <i>Principles of organic synthesis</i>. Coxon, J. M. (James Morriss), 1941- (3rd. ed.). London: Blackie Academic & Professional. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0751401264" title="Special:BookSources/978-0751401264"><bdi>978-0751401264</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/27813843">27813843</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+organic+synthesis.&rft.place=London&rft.edition=3rd.&rft.pub=Blackie+Academic+%26+Professional&rft.date=1993&rft_id=info%3Aoclcnum%2F27813843&rft.isbn=978-0751401264&rft.aulast=Chandler%29&rft.aufirst=Norman%2C+R.+O.+C.+%28Richard+Oswald&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJohnston2001" class="citation cs2">Johnston, Jeffrey N. (2001), "Chromium(VI) Oxide–3,5-Dimethylpyrazole", <i>Encyclopedia of Reagents for Organic Synthesis</i>, American Cancer Society, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289x.rc170">10.1002/047084289x.rc170</a>, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470842898" title="Special:BookSources/9780470842898"><bdi>9780470842898</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chromium%28VI%29+Oxide%E2%80%933%2C5-Dimethylpyrazole&rft.btitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.pub=American+Cancer+Society&rft.date=2001&rft_id=info%3Adoi%2F10.1002%2F047084289x.rc170&rft.isbn=9780470842898&rft.aulast=Johnston&rft.aufirst=Jeffrey+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaranZhong2001" class="citation journal cs1">Baran, Phil S.; Zhong, Yong-Li (2001-04-01). "Selective Oxidation at Carbon Adjacent to Aromatic Systems with IBX". <i>Journal of the American Chemical Society</i>. <b>123</b> (13): <span class="nowrap">3183–</span>3185. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja004218x">10.1021/ja004218x</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11457049">11457049</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Selective+Oxidation+at+Carbon+Adjacent+to+Aromatic+Systems+with+IBX&rft.volume=123&rft.issue=13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3183-%3C%2Fspan%3E3185&rft.date=2001-04-01&rft.issn=0002-7863&rft_id=info%3Apmid%2F11457049&rft_id=info%3Adoi%2F10.1021%2Fja004218x&rft.aulast=Baran&rft.aufirst=Phil+S.&rft.au=Zhong%2C+Yong-Li&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-:0-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:0_9-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWutsGreene2006" class="citation book cs1">Wuts, Peter G. M.; Greene, Theodora W. (2006). <i>Greene's Protective Groups in Organic Synthesis</i> (4th ed.). Wiley Online Library. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0470053488">10.1002/0470053488</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470053485" title="Special:BookSources/9780470053485"><bdi>9780470053485</bdi></a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:83393227">83393227</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Greene%27s+Protective+Groups+in+Organic+Synthesis&rft.edition=4th&rft.pub=Wiley+Online+Library&rft.date=2006&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A83393227%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1002%2F0470053488&rft.isbn=9780470053485&rft.aulast=Wuts&rft.aufirst=Peter+G.+M.&rft.au=Greene%2C+Theodora+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFukuzawaSatoMasamune1987" class="citation journal cs1">Fukuzawa, Akio; Sato, Hideaki; Masamune, Tadashi (1987-01-01). "Synthesis of (±)-prepinnaterpene, a bromoditerpene from the red alga Yamada". <i>Tetrahedron Letters</i>. <b>28</b> (37): <span class="nowrap">4303–</span>4306. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2800%2996491-8">10.1016/S0040-4039(00)96491-8</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Synthesis+of+%28%C2%B1%29-prepinnaterpene%2C+a+bromoditerpene+from+the+red+alga+Yamada&rft.volume=28&rft.issue=37&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4303-%3C%2Fspan%3E4306&rft.date=1987-01-01&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2800%2996491-8&rft.aulast=Fukuzawa&rft.aufirst=Akio&rft.au=Sato%2C+Hideaki&rft.au=Masamune%2C+Tadashi&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVan_HijfteLittle1985" class="citation journal cs1">Van Hijfte, Luc; Little, R. Daniel (1985-10-01). "Intramolecular 1,3-diyl trapping reactions. A formal total synthesis of (±)-coriolin". <i>The Journal of Organic Chemistry</i>. <b>50</b> (20): <span class="nowrap">3940–</span>3942. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00220a058">10.1021/jo00220a058</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Intramolecular+1%2C3-diyl+trapping+reactions.+A+formal+total+synthesis+of+%28%C2%B1%29-coriolin&rft.volume=50&rft.issue=20&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3940-%3C%2Fspan%3E3942&rft.date=1985-10-01&rft_id=info%3Adoi%2F10.1021%2Fjo00220a058&rft.issn=0022-3263&rft.aulast=Van+Hijfte&rft.aufirst=Luc&rft.au=Little%2C+R.+Daniel&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSirkeciogluKarligaTalinli2003" class="citation journal cs1">Sirkecioglu, Okan; Karliga, Bekir; Talinli, Naciye (2003-11-10). "Benzylation of alcohols by using bis[acetylacetonato]copper as catalyst". <i>Tetrahedron Letters</i>. <b>44</b> (46): <span class="nowrap">8483–</span>8485. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tetlet.2003.09.106">10.1016/j.tetlet.2003.09.106</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Benzylation+of+alcohols+by+using+bis%5Bacetylacetonato%5Dcopper+as+catalyst&rft.volume=44&rft.issue=46&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8483-%3C%2Fspan%3E8485&rft.date=2003-11-10&rft_id=info%3Adoi%2F10.1016%2Fj.tetlet.2003.09.106&rft.aulast=Sirkecioglu&rft.aufirst=Okan&rft.au=Karliga%2C+Bekir&rft.au=Talinli%2C+Naciye&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmithZhuShirakamiSfouggatakis2003" class="citation journal cs1">Smith, Amos B.; Zhu, Wenyu; Shirakami, Shohei; Sfouggatakis, Chris; Doughty, Victoria A.; Bennett, Clay S.; Sakamoto, Yasuharu (2003-03-01). "Total Synthesis of (+)-Spongistatin 1. An Effective Second-Generation Construction of an Advanced EF Wittig Salt, Fragment Union, and Final Elaboration". <i>Organic Letters</i>. <b>5</b> (5): <span class="nowrap">761–</span>764. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fol034037a">10.1021/ol034037a</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1523-7060">1523-7060</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12605509">12605509</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=Total+Synthesis+of+%28%2B%29-Spongistatin+1.+An+Effective+Second-Generation+Construction+of+an+Advanced+EF+Wittig+Salt%2C+Fragment+Union%2C+and+Final+Elaboration&rft.volume=5&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E761-%3C%2Fspan%3E764&rft.date=2003-03-01&rft.issn=1523-7060&rft_id=info%3Apmid%2F12605509&rft_id=info%3Adoi%2F10.1021%2Fol034037a&rft.aulast=Smith&rft.aufirst=Amos+B.&rft.au=Zhu%2C+Wenyu&rft.au=Shirakami%2C+Shohei&rft.au=Sfouggatakis%2C+Chris&rft.au=Doughty%2C+Victoria+A.&rft.au=Bennett%2C+Clay+S.&rft.au=Sakamoto%2C+Yasuharu&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarcoHueso-Rodríguez1988" class="citation journal cs1">Marco, José L.; Hueso-Rodríguez, Juan A. (1988-01-01). "Synthesis of optically pure 1-(3-furyl)-1,2-dihydroxyethane derivatives". <i>Tetrahedron Letters</i>. <b>29</b> (20): <span class="nowrap">2459–</span>2462. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2800%2987907-1">10.1016/S0040-4039(00)87907-1</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Synthesis+of+optically+pure+1-%283-furyl%29-1%2C2-dihydroxyethane+derivatives&rft.volume=29&rft.issue=20&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2459-%3C%2Fspan%3E2462&rft.date=1988-01-01&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2800%2987907-1&rft.aulast=Marco&rft.aufirst=Jos%C3%A9+L.&rft.au=Hueso-Rodr%C3%ADguez%2C+Juan+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakakuKamaikeTsuchiya1984" class="citation journal cs1">Takaku, Hiroshi; Kamaike, Kazuo; Tsuchiya, Hiromichi (1984-01-01). "Oligonucleotide synthesis. Part 21. Synthesis of ribooligonucleotides using the 4-methoxybenzyl group as a new protecting group for the 2′-hydroxyl group". <i>The Journal of Organic Chemistry</i>. <b>49</b> (1): <span class="nowrap">51–</span>56. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00175a010">10.1021/jo00175a010</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Oligonucleotide+synthesis.+Part+21.+Synthesis+of+ribooligonucleotides+using+the+4-methoxybenzyl+group+as+a+new+protecting+group+for+the+2%E2%80%B2-hydroxyl+group&rft.volume=49&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E51-%3C%2Fspan%3E56&rft.date=1984-01-01&rft_id=info%3Adoi%2F10.1021%2Fjo00175a010&rft.issn=0022-3263&rft.aulast=Takaku&rft.aufirst=Hiroshi&rft.au=Kamaike%2C+Kazuo&rft.au=Tsuchiya%2C+Hiromichi&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTrostWaserMeyer2007" class="citation journal cs1">Trost, Barry M.; Waser, Jerome; Meyer, Arndt (2007-11-01). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2535803">"Total Synthesis of (−)-Pseudolaric Acid B"</a>. <i>Journal of the American Chemical Society</i>. <b>129</b> (47): <span class="nowrap">14556–</span>14557. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja076165q">10.1021/ja076165q</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2535803">2535803</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17985906">17985906</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Total+Synthesis+of+%28%E2%88%92%29-Pseudolaric+Acid+B&rft.volume=129&rft.issue=47&rft.pages=%3Cspan+class%3D%22nowrap%22%3E14556-%3C%2Fspan%3E14557&rft.date=2007-11-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2535803%23id-name%3DPMC&rft.issn=0002-7863&rft_id=info%3Apmid%2F17985906&rft_id=info%3Adoi%2F10.1021%2Fja076165q&rft.aulast=Trost&rft.aufirst=Barry+M.&rft.au=Waser%2C+Jerome&rft.au=Meyer%2C+Arndt&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2535803&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMukaiyamaShiinaIwadareSaitoh1999" class="citation journal cs1">Mukaiyama, Teruaki; Shiina, Isamu; Iwadare, Hayato; Saitoh, Masahiro; Nishimura, Toshihiro; Ohkawa, Naoto; Sakoh, Hiroki; Nishimura, Koji; Tani, Yu-ichirou (1999-01-04). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F%28SICI%291521-3765%2819990104%295%3A1%3C121%3A%3AAID-CHEM121%3E3.0.CO%3B2-O">"Asymmetric Total Synthesis of Taxol\R"</a>. <i>Chemistry – A European Journal</i>. <b>5</b> (1): <span class="nowrap">121–</span>161. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F%28SICI%291521-3765%2819990104%295%3A1%3C121%3A%3AAID-CHEM121%3E3.0.CO%3B2-O">10.1002/(SICI)1521-3765(19990104)5:1<121::AID-CHEM121>3.0.CO;2-O</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1521-3765">1521-3765</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+%E2%80%93+A+European+Journal&rft.atitle=Asymmetric+Total+Synthesis+of+Taxol%5CR&rft.volume=5&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E121-%3C%2Fspan%3E161&rft.date=1999-01-04&rft_id=info%3Adoi%2F10.1002%2F%28SICI%291521-3765%2819990104%295%3A1%3C121%3A%3AAID-CHEM121%3E3.0.CO%3B2-O&rft.issn=1521-3765&rft.aulast=Mukaiyama&rft.aufirst=Teruaki&rft.au=Shiina%2C+Isamu&rft.au=Iwadare%2C+Hayato&rft.au=Saitoh%2C+Masahiro&rft.au=Nishimura%2C+Toshihiro&rft.au=Ohkawa%2C+Naoto&rft.au=Sakoh%2C+Hiroki&rft.au=Nishimura%2C+Koji&rft.au=Tani%2C+Yu-ichirou&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252F%2528SICI%25291521-3765%252819990104%25295%253A1%253C121%253A%253AAID-CHEM121%253E3.0.CO%253B2-O&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHanessianMarcotteMachaalaniHuang2003" class="citation journal cs1">Hanessian, Stephen; Marcotte, Stéphane; Machaalani, Roger; Huang, Guobin (2003-11-01). "Total Synthesis and Structural Confirmation of Malayamycin A: A Novel Bicyclic <i>C</i>-Nucleoside from Streptomyces malaysiensis". <i>Organic Letters</i>. <b>5</b> (23): <span class="nowrap">4277–</span>4280. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fol030095k">10.1021/ol030095k</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1523-7060">1523-7060</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14601979">14601979</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=Total+Synthesis+and+Structural+Confirmation+of+Malayamycin+A%3A+A+Novel+Bicyclic+C-Nucleoside+from+Streptomyces+malaysiensis&rft.volume=5&rft.issue=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4277-%3C%2Fspan%3E4280&rft.date=2003-11-01&rft.issn=1523-7060&rft_id=info%3Apmid%2F14601979&rft_id=info%3Adoi%2F10.1021%2Fol030095k&rft.aulast=Hanessian&rft.aufirst=Stephen&rft.au=Marcotte%2C+St%C3%A9phane&rft.au=Machaalani%2C+Roger&rft.au=Huang%2C+Guobin&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuehneXu1993" class="citation journal cs1">Kuehne, Martin E.; Xu, Feng (1993-12-01). "Total synthesis of strychnan and aspidospermatan alkaloids. 3. The total synthesis of (±)-strychnine". <i>The Journal of Organic Chemistry</i>. <b>58</b> (26): <span class="nowrap">7490–</span>7497. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00078a030">10.1021/jo00078a030</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Total+synthesis+of+strychnan+and+aspidospermatan+alkaloids.+3.+The+total+synthesis+of+%28%C2%B1%29-strychnine&rft.volume=58&rft.issue=26&rft.pages=%3Cspan+class%3D%22nowrap%22%3E7490-%3C%2Fspan%3E7497&rft.date=1993-12-01&rft_id=info%3Adoi%2F10.1021%2Fjo00078a030&rft.issn=0022-3263&rft.aulast=Kuehne&rft.aufirst=Martin+E.&rft.au=Xu%2C+Feng&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCainCousinsCoumbaridesSimpkins1990" class="citation journal cs1">Cain, Christian M.; Cousins, Richard P. C.; Coumbarides, Greg; Simpkins, Nigel S. (1990-01-01). "Asymmetric deprotonation of prochiral ketones using chiral lithium amide bases". <i>Tetrahedron</i>. <b>46</b> (2): <span class="nowrap">523–</span>544. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4020%2801%2985435-1">10.1016/S0040-4020(01)85435-1</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Asymmetric+deprotonation+of+prochiral+ketones+using+chiral+lithium+amide+bases&rft.volume=46&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E523-%3C%2Fspan%3E544&rft.date=1990-01-01&rft_id=info%3Adoi%2F10.1016%2FS0040-4020%2801%2985435-1&rft.aulast=Cain&rft.aufirst=Christian+M.&rft.au=Cousins%2C+Richard+P.+C.&rft.au=Coumbarides%2C+Greg&rft.au=Simpkins%2C+Nigel+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhouLiaoCook2004" class="citation journal cs1">Zhou, Hao; Liao, Xuebin; Cook, James M. (2004-01-01). "Regiospecific, Enantiospecific Total Synthesis of the 12-Alkoxy-Substituted Indole Alkaloids, (+)-12-Methoxy-Na-methylvellosimine, (+)-12-Methoxyaffinisine, and (−)-Fuchsiaefoline". <i>Organic Letters</i>. <b>6</b> (2): <span class="nowrap">249–</span>252. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fol0362212">10.1021/ol0362212</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1523-7060">1523-7060</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14723540">14723540</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=Regiospecific%2C+Enantiospecific+Total+Synthesis+of+the+12-Alkoxy-Substituted+Indole+Alkaloids%2C+%28%2B%29-12-Methoxy-Na-methylvellosimine%2C+%28%2B%29-12-Methoxyaffinisine%2C+and+%28%E2%88%92%29-Fuchsiaefoline&rft.volume=6&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E249-%3C%2Fspan%3E252&rft.date=2004-01-01&rft.issn=1523-7060&rft_id=info%3Apmid%2F14723540&rft_id=info%3Adoi%2F10.1021%2Fol0362212&rft.aulast=Zhou&rft.aufirst=Hao&rft.au=Liao%2C+Xuebin&rft.au=Cook%2C+James+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> <li id="cite_note-Parkin-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-Parkin_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRongAl-HarbiParkin2012" class="citation journal cs1">Rong, Yi; Al-Harbi, Ahmed; Parkin, Gerard (2012). "Highly Variable Zr–CH2–Ph Bond Angles in Tetrabenzylzirconium: Analysis of Benzyl Ligand Coordination Modes". <i>Organometallics</i>. <b>31</b> (23): <span class="nowrap">8208–</span>8217. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fom300820b">10.1021/om300820b</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organometallics&rft.atitle=Highly+Variable+Zr%E2%80%93CH2%E2%80%93Ph+Bond+Angles+in+Tetrabenzylzirconium%3A+Analysis+of+Benzyl+Ligand+Coordination+Modes&rft.volume=31&rft.issue=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E8208-%3C%2Fspan%3E8217&rft.date=2012&rft_id=info%3Adoi%2F10.1021%2Fom300820b&rft.aulast=Rong&rft.aufirst=Yi&rft.au=Al-Harbi%2C+Ahmed&rft.au=Parkin%2C+Gerard&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzyl+group" class="Z3988"></span></span> </li> </ol></div> <div 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.nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups729" style="padding:3px"><table class="nowraplinks hlist mw-collapsible expanded navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar 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href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a class="mw-selflink selflink">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: 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