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id="toc-Phosphonic_and_phosphinic_acids_and_their_esters-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phosphine_oxides,_imides,_and_chalcogenides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphine_oxides,_imides,_and_chalcogenides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Phosphine oxides, imides, and chalcogenides</span> </div> </a> <ul id="toc-Phosphine_oxides,_imides,_and_chalcogenides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phosphonium_salts_and_phosphoranes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphonium_salts_and_phosphoranes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Phosphonium salts and phosphoranes</span> </div> </a> <ul id="toc-Phosphonium_salts_and_phosphoranes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Organophosphorus(III)_compounds,_main_categories" 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phosphonites, and phosphinites</span> </div> </a> <ul id="toc-Phosphites,_phosphonites,_and_phosphinites-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phosphines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphines"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Phosphines</span> </div> </a> <ul id="toc-Phosphines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phosphaalkenes_and_phosphaalkynes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Phosphaalkenes_and_phosphaalkynes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Phosphaalkenes and phosphaalkynes</span> </div> </a> <ul id="toc-Phosphaalkenes_and_phosphaalkynes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Organophosphorus(0),_(I),_and_(II)_compounds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Organophosphorus(0),_(I),_and_(II)_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Organophosphorus(0), (I), and (II) compounds</span> </div> </a> <ul id="toc-Organophosphorus(0),_(I),_and_(II)_compounds-sublist" class="vector-toc-list"> </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" > <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 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Available in 31 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-31" 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">31 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%B1%D9%83%D8%A8_%D9%81%D8%B3%D9%81%D9%88%D8%B1_%D8%B9%D8%B6%D9%88%D9%8A" title="مركب فسفور عضوي – Arabic" lang="ar" hreflang="ar" data-title="مركب فسفور عضوي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Compuestu_organofosfor%C3%A1u" title="Compuestu organofosforáu – Asturian" lang="ast" hreflang="ast" data-title="Compuestu organofosforáu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Fosforlu_%C3%BCzvi_birl%C9%99%C5%9Fm%C9%99l%C9%99r" title="Fosforlu üzvi birləşmələr – Azerbaijani" lang="az" hreflang="az" data-title="Fosforlu üzvi birləşmələr" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Organofosforni_spoj" title="Organofosforni spoj – Bosnian" lang="bs" hreflang="bs" data-title="Organofosforni spoj" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Compost_organofosforat" title="Compost organofosforat – Catalan" lang="ca" hreflang="ca" data-title="Compost organofosforat" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Organick%C3%A9_slou%C4%8Deniny_fosforu" title="Organické sloučeniny fosforu – Czech" lang="cs" hreflang="cs" data-title="Organické sloučeniny fosforu" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CF%81%CE%B3%CE%B1%CE%BD%CE%B9%CE%BA%CE%AD%CF%82_%CE%B5%CE%BD%CF%8E%CF%83%CE%B5%CE%B9%CF%82_%CE%BC%CE%B5_%CF%86%CF%89%CF%83%CF%86%CF%8C%CF%81%CE%BF" title="Οργανικές ενώσεις με φωσφόρο – Greek" lang="el" hreflang="el" data-title="Οργανικές ενώσεις με φωσφόρο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Organofosforado" title="Organofosforado – Spanish" lang="es" hreflang="es" data-title="Organofosforado" 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/Organofosforo_konposatu" title="Organofosforo konposatu – Basque" lang="eu" hreflang="eu" data-title="Organofosforo konposatu" 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/%D8%AA%D8%B1%DA%A9%DB%8C%D8%A8%D8%A7%D8%AA_%D8%A2%D9%84%DB%8C_%D9%81%D8%B3%D9%81%D8%B1" title="ترکیبات آلی فسفر – Persian" lang="fa" hreflang="fa" data-title="ترکیبات آلی فسفر" 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/Compos%C3%A9_organophosphor%C3%A9" title="Composé organophosphoré – French" lang="fr" hreflang="fr" data-title="Composé organophosphoré" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Composto_organofosforado" title="Composto organofosforado – Galician" lang="gl" hreflang="gl" data-title="Composto organofosforado" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9C%A0%EA%B8%B0_%EC%9D%B8_%ED%99%94%ED%95%A9%EB%AC%BC" title="유기 인 화합물 – Korean" lang="ko" hreflang="ko" data-title="유기 인 화합물" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Organofosforni_spoj" title="Organofosforni spoj – Croatian" lang="hr" hreflang="hr" data-title="Organofosforni spoj" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Composto_organofosforico" title="Composto organofosforico – Italian" lang="it" hreflang="it" data-title="Composto organofosforico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Organofosforchemie" title="Organofosforchemie – Dutch" lang="nl" hreflang="nl" data-title="Organofosforchemie" 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/%E6%9C%89%E6%A9%9F%E3%83%AA%E3%83%B3%E5%8C%96%E5%90%88%E7%89%A9" title="有機リン化合物 – Japanese" lang="ja" hreflang="ja" data-title="有機リン化合物" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Organofosforat" title="Organofosforat – Occitan" lang="oc" hreflang="oc" data-title="Organofosforat" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Fosfororganik_birikmalar" title="Fosfororganik birikmalar – Uzbek" lang="uz" hreflang="uz" data-title="Fosfororganik birikmalar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Zwi%C4%85zki_fosforoorganiczne" title="Związki fosforoorganiczne – Polish" lang="pl" hreflang="pl" data-title="Związki fosforoorganiczne" 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/Composto_organofosforado" title="Composto organofosforado – Portuguese" lang="pt" hreflang="pt" data-title="Composto organofosforado" 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/Compus_organofosforat" title="Compus organofosforat – Romanian" lang="ro" hreflang="ro" data-title="Compus organofosforat" 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%A4%D0%BE%D1%81%D1%84%D0%BE%D1%80%D0%BE%D1%80%D0%B3%D0%B0%D0%BD%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D1%81%D0%BE%D0%B5%D0%B4%D0%B8%D0%BD%D0%B5%D0%BD%D0%B8%D1%8F" title="Фосфорорганические соединения – Russian" lang="ru" hreflang="ru" data-title="Фосфорорганические соединения" 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/Organofosfor" title="Organofosfor – Serbian" lang="sr" hreflang="sr" data-title="Organofosfor" 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/Organofosfor" title="Organofosfor – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Organofosfor" 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-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%B0%E0%AE%BF%E0%AE%AE%E0%AE%AA%E0%AE%BE%E0%AE%9A%E0%AF%81%E0%AE%AA%E0%AE%B0%E0%AE%9A%E0%AF%81_%E0%AE%9A%E0%AF%87%E0%AE%B0%E0%AF%8D%E0%AE%AE%E0%AE%99%E0%AF%8D%E0%AE%95%E0%AE%B3%E0%AF%8D" title="கரிமபாசுபரசு சேர்மங்கள் – Tamil" lang="ta" hreflang="ta" data-title="கரிமபாசுபரசு சேர்மங்கள்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Organofosforlar" title="Organofosforlar – Turkish" lang="tr" hreflang="tr" data-title="Organofosforlar" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%BE%D1%81%D1%84%D0%BE%D1%80%D0%BE%D1%80%D0%B3%D0%B0%D0%BD%D1%96%D1%87%D0%BD%D1%96_%D1%81%D0%BF%D0%BE%D0%BB%D1%83%D0%BA%D0%B8" title="Фосфорорганічні сполуки – Ukrainian" lang="uk" hreflang="uk" data-title="Фосфорорганічні сполуки" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E6%9C%89%E6%A9%9F%E7%A3%B7" title="有機磷 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="有機磷" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E6%9C%89%E6%A9%9F%E7%A3%B7%E5%8C%96%E5%90%88%E7%89%A9" title="有機磷化合物 – Cantonese" lang="yue" hreflang="yue" data-title="有機磷化合物" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9C%89%E6%9C%BA%E7%A3%B7%E5%8C%96%E5%90%88%E7%89%A9" title="有机磷化合物 – Chinese" lang="zh" hreflang="zh" data-title="有机磷化合物" 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/Q2182492#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound with at least one covalent carbon–phosphorus bond</div> <p><b>Organophosphorus chemistry</b> is the scientific study of the synthesis and properties of <b>organophosphorus compounds</b>, which are <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> containing <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a>.<sup id="cite_ref-MWU_1-0" class="reference"><a href="#cite_note-MWU-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They are used primarily in <a href="/wiki/Pest_control" title="Pest control">pest control</a> as an alternative to <a href="/wiki/Chlorinated_hydrocarbons" class="mw-redirect" title="Chlorinated hydrocarbons">chlorinated hydrocarbons</a> that persist in the environment. Some organophosphorus compounds are highly effective <a href="/wiki/Insecticide" title="Insecticide">insecticides</a>, although some are extremely toxic to humans, including <a href="/wiki/Sarin" title="Sarin">sarin</a> and <a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a> nerve agents.<sup id="cite_ref-Lewis1998_2-0" class="reference"><a href="#cite_note-Lewis1998-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Phosphorus, like <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>, is in <a href="/wiki/Pnictogen" title="Pnictogen">group 15</a> of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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><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> The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic <a href="/wiki/Substituent" title="Substituent">substituent</a>, but need not have a direct phosphorus-carbon (P-C) bond.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2017)">citation needed</span></a></i>]</sup> Thus a large proportion of pesticides (e.g., <a href="/wiki/Malathion" title="Malathion">malathion</a>), are often included in this class of compounds. </p><p>Phosphorus can adopt a variety of <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation states</a>, and it is general to classify organophosphorus compounds based on their being derivatives of phosphorus(V) vs phosphorus(III), which are the predominant classes of compounds. In a descriptive but only intermittently used nomenclature, phosphorus compounds are identified by their <a href="/wiki/Coordination_number" title="Coordination number">coordination number</a> <a href="/wiki/Sigma_(letter)" class="mw-redirect" title="Sigma (letter)">σ</a> and their <a href="/wiki/Valence_(chemistry)" title="Valence (chemistry)">valency</a> <a href="/wiki/Lambda" title="Lambda">λ</a>. In this system, a phosphine is a σ<sup>3</sup>λ<sup>3</sup> compound. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Organophosphorus(V)_compounds,_main_categories"><span id="Organophosphorus.28V.29_compounds.2C_main_categories"></span>Organophosphorus(V) compounds, main categories</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=1" title="Edit section: Organophosphorus(V) compounds, main categories"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Phosphate_esters_and_amides">Phosphate esters and amides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=2" title="Edit section: Phosphate esters and amides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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">Main article: <a href="/wiki/Organophosphate" title="Organophosphate">Organophosphate</a></div> <p><a href="/wiki/Phosphate_ester" class="mw-redirect" title="Phosphate ester">Phosphate esters</a> have the general structure P(=O)(OR)<sub>3</sub> feature P(V). Such species are of technological importance as <a href="/wiki/Flame_retardant" title="Flame retardant">flame retardant</a> agents, and <a href="/wiki/Plasticizer" title="Plasticizer">plasticizers</a>. Lacking a P−C bond, these compounds are in the technical sense not organophosphorus compounds but esters of phosphoric acid. Many derivatives are found in nature, such as <a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">phosphatidylcholine</a>. Phosphate ester are synthesized by <a href="/wiki/Alcoholysis" class="mw-redirect" title="Alcoholysis">alcoholysis</a> of phosphorus oxychloride. A variety of mixed amido-alkoxo derivatives are known, one medically significant example being the anti-cancer drug <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>. Also derivatives containing the thiophosphoryl group (P=S) include the pesticide <a href="/wiki/Malathion" title="Malathion">malathion</a>. The organophosphates prepared on the largest scale are the <a href="/wiki/Zinc_dithiophosphate" title="Zinc dithiophosphate">zinc dithiophosphates</a>, as additives for motor oil. Several million kilograms of this <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> are produced annually by the reaction of phosphorus pentasulfide with alcohols.<sup id="cite_ref-Ullmann_6-0" class="reference"><a href="#cite_note-Ullmann-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:PhosphatesView.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/PhosphatesView.png/850px-PhosphatesView.png" decoding="async" width="850" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/PhosphatesView.png/1275px-PhosphatesView.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/PhosphatesView.png/1700px-PhosphatesView.png 2x" data-file-width="4137" data-file-height="530" /></a><figcaption>Illustrative organophosphates and related compounds: phosphatidylcholine, <a href="/wiki/Triphenylphosphate" class="mw-redirect" title="Triphenylphosphate">triphenylphosphate</a>, <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>, <a href="/wiki/Parathion" title="Parathion">parathion</a>, and <a href="/wiki/Zinc_dithiophosphate" title="Zinc dithiophosphate">zinc dithiophosphate</a>.</figcaption></figure> <p>Phosphoryl thioates are thermodynamically much stabler than thiophosphates, which can rearrange at high temperature or with a catalytic alkylant to the former:<sup id="cite_ref-Sulf_7-0" class="reference"><a href="#cite_note-Sulf-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 73–76">: 73–76 </span></sup> </p> <dl><dd>SP(OR)<sub>3</sub> → OP(OR)<sub>2</sub>SR</dd></dl> <p>In the environment, all these phosphorus(V) compounds break down via <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> to eventually afford <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> and the organic alcohol or amine from which they are derived. </p> <div class="mw-heading mw-heading3"><h3 id="Phosphonic_and_phosphinic_acids_and_their_esters">Phosphonic and phosphinic acids and their esters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=3" title="Edit section: Phosphonic and phosphinic acids and their esters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> and <a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></div> <p><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonates</a> are esters of phosphonic acid and have the general formula RP(=O)(OR')<sub>2</sub>. Phosphonates have many technical applications, a well-known member being <a href="/wiki/Glyphosate" title="Glyphosate">glyphosate</a>, better known as Roundup. With the formula (HO)<sub>2</sub>P(O)CH<sub>2</sub>NHCH<sub>2</sub>CO<sub>2</sub>H, this derivative of <a href="/wiki/Glycine" title="Glycine">glycine</a> is one of the most widely used herbicides. <a href="/wiki/Bisphosphonate" title="Bisphosphonate">Bisphosphonates</a> are a class of drugs to treat <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>. The nerve gas agent <a href="/wiki/Sarin" title="Sarin">sarin</a>, containing both C–P and F–P bonds, is a phosphonate. </p><p>Phosphinates feature <i>two</i> P–C bonds, with the general formula R<sub>2</sub>P(=O)(OR'). A commercially significant member is the herbicide <a href="/wiki/Glufosinate" title="Glufosinate">glufosinate</a>. Similar to glyphosate mentioned above, it has the structure CH<sub>3</sub>P(O)(OH)CH<sub>2</sub>CH<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:PhosphonatesEtc.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/PhosphonatesEtc.png/850px-PhosphonatesEtc.png" decoding="async" width="850" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/PhosphonatesEtc.png/1275px-PhosphonatesEtc.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/PhosphonatesEtc.png/1700px-PhosphonatesEtc.png 2x" data-file-width="3979" data-file-height="615" /></a><figcaption>Illustrative examples of phosphonates and phosphinates in the order shown: Sarin (phosphonate), <a href="/wiki/Glyphosate" title="Glyphosate">Glyphosate</a> (phosphonate), <a href="/wiki/Fosfomycin" title="Fosfomycin">fosfomycin</a> (phosphonate), <a href="/wiki/Zoledronic_acid" title="Zoledronic acid">zoledronic acid</a> (phosphonate), and <a href="/wiki/Glufosinate" title="Glufosinate">Glufosinate</a> (phosphinate). In aqueous solution, phosphonic acids ionize to give the corresponding organophosphonates.</figcaption></figure></dd></dl> <p>The <a href="/wiki/Michaelis%E2%80%93Arbuzov_reaction" title="Michaelis–Arbuzov reaction">Michaelis–Arbuzov reaction</a> is the main method for the synthesis of these compounds. For example, dimethylmethylphosphonate (see figure above) arises from the rearrangement of <a href="/wiki/Trimethylphosphite" class="mw-redirect" title="Trimethylphosphite">trimethylphosphite</a>, which is catalyzed by <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">methyl iodide</a>. In the <a href="/wiki/Horner%E2%80%93Wadsworth%E2%80%93Emmons_reaction" title="Horner–Wadsworth–Emmons reaction">Horner–Wadsworth–Emmons reaction</a> and the <a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a>, phosphonates are used in reactions with <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> compounds. The <a href="/wiki/Kabachnik%E2%80%93Fields_reaction" title="Kabachnik–Fields reaction">Kabachnik–Fields reaction</a> is a method for the preparation of aminophosphonates. These compounds contain a very inert bond between phosphorus and carbon. Consequently, they hydrolyze to give phosphonic and phosphinic acid derivatives, but not phosphate. </p> <div class="mw-heading mw-heading3"><h3 id="Phosphine_oxides,_imides,_and_chalcogenides"><span id="Phosphine_oxides.2C_imides.2C_and_chalcogenides"></span>Phosphine oxides, imides, and chalcogenides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=4" title="Edit section: Phosphine oxides, imides, and chalcogenides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></div> <p>Phosphine oxides (designation σ<sup>4</sup>λ<sup>5</sup>) have the general structure R<sub>3</sub>P=O with formal oxidation state V. Phosphine oxides form <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> and some are therefore soluble in water. The P=O bond is very polar with a <a href="/wiki/Molecular_dipole_moment" class="mw-redirect" title="Molecular dipole moment">dipole moment</a> of 4.51 D for <a href="/wiki/Triphenylphosphine_oxide" title="Triphenylphosphine oxide">triphenylphosphine oxide</a>. </p><p>Compounds related to phosphine oxides include <a href="/wiki/Phosphine_imide" title="Phosphine imide">phosphine imides</a> (R<sub>3</sub>PNR') and related <a href="/wiki/Chalcogenide" title="Chalcogenide">chalcogenides</a> (R<sub>3</sub>PE, where E = <a href="/wiki/Sulfur" title="Sulfur">S</a>, <a href="/wiki/Selenium" title="Selenium">Se</a>, <a href="/wiki/Tellurium" title="Tellurium">Te</a>). These compounds are some of the most thermally stable organophosphorus compounds. In general, they are less basic than the corresponding phosphine oxides, which can adduce to thiophosphoryl halides:<sup id="cite_ref-Sulf_7-1" class="reference"><a href="#cite_note-Sulf-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 73">: 73 </span></sup> </p> <dl><dd>R<sub>3</sub>PO + X<sub>3</sub>PS → R<sub>3</sub>P<sup>+</sup>–O–P<sup>+</sup>X<sub>2</sub>–S<sup>−</sup> + X<sup>−</sup></dd></dl> <p>Some phosphorus sulfides can undergo a reverse <a href="/w/index.php?title=Arbuzov_rearrangement&action=edit&redlink=1" class="new" title="Arbuzov rearrangement (page does not exist)">Arbuzov rearrangement</a> to a dialkylthiophosphinate ester.<sup id="cite_ref-Sulf_7-2" class="reference"><a href="#cite_note-Sulf-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 55">: 55 </span></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Phosphonium_salts_and_phosphoranes">Phosphonium salts and phosphoranes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=5" title="Edit section: Phosphonium salts and phosphoranes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Compounds with the formula [PR<sub>4</sub><sup>+</sup>]X<sup>−</sup> comprise the <a href="/wiki/Phosphonium" title="Phosphonium">phosphonium salts</a>. These species are tetrahedral phosphorus(V) compounds. From the commercial perspective, the most important member is <a href="/wiki/Tetrakis(hydroxymethyl)phosphonium_chloride" title="Tetrakis(hydroxymethyl)phosphonium chloride">tetrakis(hydroxymethyl)phosphonium chloride</a>, [P(CH<sub>2</sub>OH)<sub>4</sub>]Cl, which is used as a fire retardant in <a href="/wiki/Textile" title="Textile">textiles</a>. Approximately 2M kg are produced annually of the chloride and the related sulfate.<sup id="cite_ref-Ullmann_6-1" class="reference"><a href="#cite_note-Ullmann-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> They are generated by the reaction of phosphine with <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> in the presence of the mineral acid: </p> <dl><dd>PH<sub>3</sub> + HX + 4 CH<sub>2</sub>O → [P(CH<sub>2</sub>OH)<sub>4</sub><sup>+</sup>]X<sup>−</sup></dd></dl> <p>A variety of phosphonium salts can be prepared by <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> and <a href="/wiki/Arylation" class="mw-redirect" title="Arylation">arylation</a> of organophosphines: </p> <dl><dd>PR<sub>3</sub> + R'X → [PR<sub>3</sub>R'<sup>+</sup>]X<sup>−</sup></dd></dl> <p>The methylation of triphenylphosphine is the first step in the preparation of the Wittig reagent. </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:PhosphoranePh5.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/PhosphoranePh5.png/580px-PhosphoranePh5.png" decoding="async" width="580" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/PhosphoranePh5.png/870px-PhosphoranePh5.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/PhosphoranePh5.png/1160px-PhosphoranePh5.png 2x" data-file-width="2604" data-file-height="503" /></a><figcaption>Illustrative phosphorus(V) compounds: the phosphonium ion P(CH<sub>2</sub>OH)<sub>4</sub><sup>+</sup>, two resonance structures for the <a href="/wiki/Wittig_reagent" class="mw-redirect" title="Wittig reagent">Wittig reagent</a> Ph<sub>3</sub>PCH<sub>2</sub>, and pentaphenylphosphorane, a rare pentaorganophophorus compound.</figcaption></figure></dd></dl> <p>The parent <a href="/wiki/Phosphorane" class="mw-redirect" title="Phosphorane">phosphorane</a> (σ<sup>5</sup>λ<sup>5</sup>) is PH<sub>5</sub>, which is unknown.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2018)">citation needed</span></a></i>]</sup> Related compounds containing both halide and organic substituents on phosphorus are fairly common. Those with five organic substituents are rare, although P(C<sub>6</sub>H<sub>5</sub>)<sub>5</sub> is known, being derived from <a href="/wiki/Tetraphenylphosphonium" class="mw-redirect" title="Tetraphenylphosphonium">P(C<sub>6</sub>H<sub>5</sub>)<sub>4</sub><sup>+</sup></a> by reaction with <a href="/wiki/Phenyllithium" title="Phenyllithium">phenyllithium</a>. </p><p>Phosphorus <a href="/wiki/Ylide" title="Ylide">ylides</a> are unsaturated phosphoranes, known as <a href="/wiki/Wittig_reagent" class="mw-redirect" title="Wittig reagent">Wittig reagents</a>, e.g. CH<sub>2</sub>P(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>. These compounds feature tetrahedral phosphorus(V) and are considered relatives of phosphine oxides. They also are derived from phosphonium salts, but by deprotonation not alkylation. </p> <div class="mw-heading mw-heading2"><h2 id="Organophosphorus(III)_compounds,_main_categories"><span id="Organophosphorus.28III.29_compounds.2C_main_categories"></span>Organophosphorus(III) compounds, main categories</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=6" title="Edit section: Organophosphorus(III) compounds, main categories"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Phosphites,_phosphonites,_and_phosphinites"><span id="Phosphites.2C_phosphonites.2C_and_phosphinites"></span>Phosphites, phosphonites, and phosphinites</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=7" title="Edit section: Phosphites, phosphonites, and phosphinites"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite ester</a>, <a href="/wiki/Phosphonite" title="Phosphonite">Phosphonite</a>, and <a href="/wiki/Phosphinite" title="Phosphinite">Phosphinite</a></div> <p>Phosphites, sometimes called <a href="/wiki/Phosphite_ester" title="Phosphite ester">phosphite esters</a>, have the general structure P(OR)<sub>3</sub> with oxidation state +3. Such species arise from the alcoholysis of phosphorus trichloride: </p> <dl><dd>PCl<sub>3</sub> + 3 ROH → P(OR)<sub>3</sub> + 3 HCl</dd></dl> <p>The reaction is general, thus a vast number of such species are known. Phosphites are employed in the <a href="/wiki/Perkow_reaction" title="Perkow reaction">Perkow reaction</a> and the <a href="/wiki/Michaelis%E2%80%93Arbuzov_reaction" title="Michaelis–Arbuzov reaction">Michaelis–Arbuzov reaction</a>. They also serve as ligands in organometallic chemistry. </p><p>Intermediate between phosphites and phosphines are <a href="/wiki/Phosphonite" title="Phosphonite">phosphonites</a> (P(OR)<sub>2</sub>R') and <a href="/wiki/Phosphinite" title="Phosphinite">phosphinite</a> (P(OR)R'<sub>2</sub>). Such species arise via alcoholysis reactions of the corresponding phosphonous and phosphinous chlorides ((PCl<sub>2</sub>R') and (PClR'<sub>2</sub>) , respectively). The latter are produced by reaction of a <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a> with a <a href="/wiki/Poor_metal" class="mw-redirect" title="Poor metal">poor metal</a>-alkyl complex, e.g. <a href="/wiki/Organomercury" class="mw-redirect" title="Organomercury">organomercury</a>, <a href="/wiki/Organolead" class="mw-redirect" title="Organolead">organolead</a>, or a mixed <a href="/wiki/Lithium" title="Lithium">lithium</a>-<a href="/wiki/Organoaluminum" class="mw-redirect" title="Organoaluminum">organoaluminum</a> compound.<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-heading3"><h3 id="Phosphines">Phosphines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=8" title="Edit section: Phosphines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Organophosphine" title="Organophosphine">Organophosphine</a></div> <p>The parent compound of the phosphines is PH<sub>3</sub>, called <a href="/wiki/Phosphine" title="Phosphine">phosphine</a> in the US and British Commonwealth, but phosphane elsewhere.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Replacement of one or more hydrogen centers by an organic substituents (alkyl, aryl), gives PH<sub>3−x</sub>R<sub>x</sub>, an organophosphine, generally referred to as phosphines. </p><p>From the commercial perspective, the most important phosphine is <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a>, several million kilograms being produced annually. It is prepared from the reaction of <a href="/wiki/Chlorobenzene" title="Chlorobenzene">chlorobenzene</a>, <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">PCl<sub>3</sub></a>, and sodium.<sup id="cite_ref-Ullmann_6-2" class="reference"><a href="#cite_note-Ullmann-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Phosphines of a more specialized nature are usually prepared by other routes.<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> Phosphorus halides undergo <a href="/wiki/Nucleophilic_displacement" class="mw-redirect" title="Nucleophilic displacement">nucleophilic displacement</a> by organometallic reagents such as <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a>. Organophosphines are nucleophiles and <a href="/wiki/Ligand" title="Ligand">ligands</a>. Two major applications are as reagents in the <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a> and as supporting <a href="/wiki/Phosphine_ligand" class="mw-redirect" title="Phosphine ligand">phosphine ligands</a> in <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a>. </p><p>Their nucleophilicity is evidenced by their reactions with <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a> to give <a href="/wiki/Phosphonium_salt" class="mw-redirect" title="Phosphonium salt">phosphonium salts</a>. Phosphines are <a href="/wiki/Organocatalysis" title="Organocatalysis">nucleophilic catalysts</a> in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>, e.g. the <a href="/wiki/Rauhut%E2%80%93Currier_reaction" title="Rauhut–Currier reaction">Rauhut–Currier reaction</a> and <a href="/wiki/Baylis-Hillman_reaction" class="mw-redirect" title="Baylis-Hillman reaction">Baylis-Hillman reaction</a>. Phosphines are <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agents</a>, as illustrated in the <a href="/wiki/Staudinger_reduction" class="mw-redirect" title="Staudinger reduction">Staudinger reduction</a> for the conversion of organic azides to amines and in the <a href="/wiki/Mitsunobu_reaction" title="Mitsunobu reaction">Mitsunobu reaction</a> for converting alcohols into esters. In these processes, the phosphine is oxidized to phosphorus(V). Phosphines have also been found to reduce activated carbonyl groups, for instance the reduction of an α-keto ester to an α-hydroxy ester.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Phosphaalkenes_and_phosphaalkynes">Phosphaalkenes and phosphaalkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=9" title="Edit section: Phosphaalkenes and phosphaalkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a> and <a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></div> <p>Compounds with carbon phosphorus(III) multiple bonds are called <a href="/wiki/Phosphaalkene" title="Phosphaalkene">phosphaalkenes</a> (R<sub>2</sub>C=PR) and <a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">phosphaalkynes</a> (RC≡P). They are similar in structure, but not in reactivity, to <a href="/wiki/Imine" title="Imine">imines</a> (R<sub>2</sub>C=NR) and <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> (RC≡N), respectively. In the compound <a href="/wiki/Phosphorine" title="Phosphorine">phosphorine</a>, one carbon atom in benzene is replaced by phosphorus. Species of this type are relatively rare but for that reason are of interest to researchers. A general method for the synthesis of phosphaalkenes is by <a href="/wiki/Elimination_reaction" title="Elimination reaction">1,2-elimination</a> of suitable precursors, initiated thermally or by base such as <a href="/wiki/DBU_(chemistry)" class="mw-redirect" title="DBU (chemistry)">DBU</a>, <a href="/wiki/DABCO" title="DABCO">DABCO</a>, or <a href="/wiki/Triethylamine" title="Triethylamine">triethylamine</a>: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:PhosphaalkeneGeneral.png" class="mw-file-description" title="Phosphaalkene general method"><img alt="Phosphaalkene general method" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/PhosphaalkeneGeneral.png/400px-PhosphaalkeneGeneral.png" decoding="async" width="400" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/PhosphaalkeneGeneral.png/600px-PhosphaalkeneGeneral.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/PhosphaalkeneGeneral.png/800px-PhosphaalkeneGeneral.png 2x" data-file-width="858" data-file-height="138" /></a></span></dd></dl> <p><a href="/wiki/Thermolysis" class="mw-redirect" title="Thermolysis">Thermolysis</a> of Me<sub>2</sub>PH generates CH<sub>2</sub>=PMe, an unstable species in the condensed phase. </p> <div class="mw-heading mw-heading2"><h2 id="Organophosphorus(0),_(I),_and_(II)_compounds"><span id="Organophosphorus.280.29.2C_.28I.29.2C_and_.28II.29_compounds"></span>Organophosphorus(0), (I), and (II) compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=10" title="Edit section: Organophosphorus(0), (I), and (II) compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Compounds where phosphorus exists in a formal oxidation state of less than III are uncommon, but examples are known for each class. Organophosphorus(0) species are debatably illustrated by the carbene adducts, [P(NHC)]<sub>2</sub>, where NHC is an <a href="/wiki/Persistent_carbene" title="Persistent carbene">N-heterocyclic carbene</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> With the formulae (RP)<sub>n</sub> and (R<sub>2</sub>P)<sub>2</sub>, respectively, <a href="/wiki/Cyclophosphines" class="mw-redirect" title="Cyclophosphines">compounds of phosphorus(I)</a> and (II) are generated by reduction of the related organophosphorus(III) chlorides: </p> <dl><dd>5 <a href="/wiki/Dichlorophenylphosphine" title="Dichlorophenylphosphine">PhPCl<sub>2</sub></a> + 5 Mg → (PhP)<sub>5</sub> + 5 MgCl<sub>2</sub></dd> <dd>2 <a href="/wiki/Chlorodiphenylphosphine" title="Chlorodiphenylphosphine">Ph<sub>2</sub>PCl</a> + Mg → Ph<sub>2</sub>P-PPh<sub>2</sub> + MgCl<sub>2</sub></dd></dl> <p><a href="/wiki/Diphosphene" title="Diphosphene">Diphosphenes</a>, with the formula R<sub>2</sub>P<sub>2</sub>, formally contain phosphorus-phosphorus double bonds. These phosphorus(I) species are rare but are stable provided that the organic substituents are large enough to prevent <a href="/wiki/Catenation" title="Catenation">catenation</a>. Bulky substituents also <a href="/wiki/Stable_phosphorus_radicals" title="Stable phosphorus radicals">stabilize phosphorus radicals</a>. </p><p>Many <a href="/wiki/Mixed-valence" class="mw-redirect" title="Mixed-valence">mixed-valence</a> compounds are known, e.g. the cage P<sub>7</sub>(CH<sub>3</sub>)<sub>3</sub>. </p> <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=Organophosphorus_chemistry&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Activity-based_proteomics" title="Activity-based proteomics">Activity-based proteomics</a>—A branch of biochemistry that often relies on organophosphorus probes to interrogate enzyme activities</li> <li><a href="/wiki/Bihar_school_meal_poisoning_incident" title="Bihar school meal poisoning incident">Bihar school meal poisoning incident</a></li> <li><a href="/wiki/Organophosphates" class="mw-redirect" title="Organophosphates">Organophosphates</a></li> <li><a href="/wiki/Organophosphites" class="mw-redirect" title="Organophosphites">Organophosphites</a></li> <li><a href="/wiki/Organothiophosphates" class="mw-redirect" title="Organothiophosphates">Organothiophosphates</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=Organophosphorus_chemistry&action=edit&section=12" 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"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-MWU-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-MWU_1-0">^</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="CITEREFMerriam-Webster" class="citation cs2"><a href="/wiki/Merriam-Webster" title="Merriam-Webster">Merriam-Webster</a>, <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200525084504/https://unabridged.merriam-webster.com/subscriber/login?redirect_to=%2Funabridged%2F"><i>Merriam-Webster's Unabridged Dictionary</i></a>, Merriam-Webster, archived from <a rel="nofollow" class="external text" href="http://unabridged.merriam-webster.com/unabridged/">the original</a> on 2020-05-25<span class="reference-accessdate">, retrieved <span class="nowrap">2015-12-17</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Merriam-Webster%27s+Unabridged+Dictionary&rft.pub=Merriam-Webster&rft.au=Merriam-Webster&rft_id=http%3A%2F%2Funabridged.merriam-webster.com%2Funabridged%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-Lewis1998-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Lewis1998_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLewis,_Robert_Alan1998" class="citation book cs1">Lewis, Robert Alan (1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=caTqdbD7j4AC&pg=PA763"><i>Lewisʼ Dictionary of Toxicology</i></a>. CRC Lewis. p. 763. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-56670-223-2" title="Special:BookSources/978-1-56670-223-2"><bdi>978-1-56670-223-2</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">18 July</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lewis%CA%BC+Dictionary+of+Toxicology&rft.pages=763&rft.pub=CRC+Lewis&rft.date=1998&rft.isbn=978-1-56670-223-2&rft.au=Lewis%2C+Robert+Alan&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcaTqdbD7j4AC%26pg%3DPA763&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">Dillon, K. B.; Mathey, F.; Nixon, J. F. (1997) <i>Phosphorus. The Carbon Copy</i>; John Wiley & Sons, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-97360-2" title="Special:BookSources/0-471-97360-2">0-471-97360-2</a></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">Quin, L. D. (2000) <i>A Guide to Organophosphorus Chemistry</i>; John Wiley & Sons, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-31824-8" title="Special:BookSources/0-471-31824-8">0-471-31824-8</a></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">Racke, K.D. (1992). "Degradation of organophosphorus insecticides in environmental matrices", pp. 47–73 in: Chambers, J.E., Levi, P.E. (eds.), Organophosphates: Chemistry, Fate, and Effects. Academic Press, San Diego, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0121673456" title="Special:BookSources/0121673456">0121673456</a>.</span> </li> <li id="cite_note-Ullmann-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_6-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSvara,_JürgenWeferling,_NorbertHofmann,_Thomas2006" class="citation book cs1">Svara, Jürgen; Weferling, Norbert & Hofmann, Thomas (2006). "Phosphorus Compounds, Organic". <i>Ullmann's Encyclopedia of Industrial Chemistry</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.a19_545.pub2">10.1002/14356007.a19_545.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Phosphorus+Compounds%2C+Organic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F14356007.a19_545.pub2&rft.isbn=978-3527306732&rft.au=Svara%2C+J%C3%BCrgen&rft.au=Weferling%2C+Norbert&rft.au=Hofmann%2C+Thomas&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-Sulf-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Sulf_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Sulf_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Sulf_7-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlmasi1971" class="citation book cs1">Almasi, Lucreţia (1971). "The Sulfur–Phosphorus Bond". In Senning, Alexander (ed.). <i>Sulfur in Organic and Inorganic Chemistry</i>. Vol. 1. New York: Marcel Dekker. pp. 39–106. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8247-1615-9" title="Special:BookSources/0-8247-1615-9"><bdi>0-8247-1615-9</bdi></a>. <a href="/wiki/LCCN_(identifier)" class="mw-redirect" title="LCCN (identifier)">LCCN</a> <a rel="nofollow" class="external text" href="https://lccn.loc.gov/70-154612">70-154612</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Sulfur%26ndash%3BPhosphorus+Bond&rft.btitle=Sulfur+in+Organic+and+Inorganic+Chemistry&rft.place=New+York&rft.pages=39-106&rft.pub=Marcel+Dekker&rft.date=1971&rft_id=info%3Alccn%2F70-154612&rft.isbn=0-8247-1615-9&rft.aulast=Almasi&rft.aufirst=Lucre%C5%A3ia&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" 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="CITEREFEngelCohen2004" class="citation book cs1">Engel, Robert; Cohen, JaimeLee Iolani (2004). <i>Synthesis of Carbon-Phosphorus Bonds</i> (2 ed.). Boca Raton: <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. §4.3.2.1–7. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8493-1617-0" title="Special:BookSources/0-8493-1617-0"><bdi>0-8493-1617-0</bdi></a>. <a href="/wiki/LCCN_(identifier)" class="mw-redirect" title="LCCN (identifier)">LCCN</a> <a rel="nofollow" class="external text" href="https://lccn.loc.gov/2003060796">2003060796</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Synthesis+of+Carbon-Phosphorus+Bonds&rft.place=Boca+Raton&rft.pages=-4.3.2.1-7&rft.edition=2&rft.pub=CRC+Press&rft.date=2004&rft_id=info%3Alccn%2F2003060796&rft.isbn=0-8493-1617-0&rft.aulast=Engel&rft.aufirst=Robert&rft.au=Cohen%2C+JaimeLee+Iolani&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/P04548.html">phosphanes</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.P04548">10.1351/goldbook.P04548</a></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="CITEREFDowningSmith2003" class="citation journal cs1">Downing, J.H.; Smith, M.B. (2003). "Phosphorus Ligands". <i>Comprehensive Coordination Chemistry II</i>. <b>2003</b>: 253–296. <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%2FB0-08-043748-6%2F01049-5">10.1016/B0-08-043748-6/01049-5</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780080437484" title="Special:BookSources/9780080437484"><bdi>9780080437484</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comprehensive+Coordination+Chemistry+II&rft.atitle=Phosphorus+Ligands&rft.volume=2003&rft.pages=253-296&rft.date=2003&rft_id=info%3Adoi%2F10.1016%2FB0-08-043748-6%2F01049-5&rft.isbn=9780080437484&rft.aulast=Downing&rft.aufirst=J.H.&rft.au=Smith%2C+M.B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" 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="CITEREFZhangShi2006" class="citation journal cs1">Zhang, W.; Shi, M. (2006). "Reduction of activated carbonyl groups by alkyl phosphines: formation of α-hydroxy esters and ketones". <i><a href="/wiki/Chemical_Communications" class="mw-redirect" title="Chemical Communications">Chem. Commun.</a></i> <b>2006</b> (11): 1218–1220. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb516467b">10.1039/b516467b</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/16518496">16518496</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Commun.&rft.atitle=Reduction+of+activated+carbonyl+groups+by+alkyl+phosphines%3A+formation+of+%CE%B1-hydroxy+esters+and+ketones&rft.volume=2006&rft.issue=11&rft.pages=1218-1220&rft.date=2006&rft_id=info%3Adoi%2F10.1039%2Fb516467b&rft_id=info%3Apmid%2F16518496&rft.aulast=Zhang&rft.aufirst=W.&rft.au=Shi%2C+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" 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="CITEREFWangXieWeiKing2008" class="citation journal cs1">Wang, Yuzhong; Xie, Yaoming; Wei, Pingrong; King, R. Bruce; Schaefer, Iii; Schleyer, Paul v. R.; Robinson, Gregory H. (2008). "Carbene-Stabilized Diphosphorus". <i>Journal of the American Chemical Society</i>. <b>130</b> (45): 14970–1. <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%2Fja807828t">10.1021/ja807828t</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/18937460">18937460</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=Carbene-Stabilized+Diphosphorus&rft.volume=130&rft.issue=45&rft.pages=14970-1&rft.date=2008&rft_id=info%3Adoi%2F10.1021%2Fja807828t&rft_id=info%3Apmid%2F18937460&rft.aulast=Wang&rft.aufirst=Yuzhong&rft.au=Xie%2C+Yaoming&rft.au=Wei%2C+Pingrong&rft.au=King%2C+R.+Bruce&rft.au=Schaefer%2C+Iii&rft.au=Schleyer%2C+Paul+v.+R.&rft.au=Robinson%2C+Gregory+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganophosphorus+chemistry" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organophosphorus_chemistry&action=edit&section=13" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Organophosphorus chemistry at <a rel="nofollow" class="external text" href="http://users.ox.ac.uk/~mwalter/web_05/resources/phos_chem/org_phosph_chem.shtml">users.ox.ac.uk</a></li> <li>Organophosphorus chemistry at <a rel="nofollow" class="external text" href="http://www.chem.wisc.edu/areas/reich/chem842/_chem842-09-phosphorus.htm">www.chem.wisc.edu</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20131111065238/http://fluorine.ch.man.ac.uk/research/p31calc.php">NMR predictor for organophosphorus compound chemical shifts</a> from <a href="/wiki/Alan_Brisdon" title="Alan Brisdon">Alan Brisdon</a>'s Research Group</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output 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href="/wiki/Template:Organophosphorus" title="Template:Organophosphorus"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organophosphorus" title="Template talk:Organophosphorus"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organophosphorus" title="Special:EditPage/Template:Organophosphorus"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Organophosphorus" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Organophosphorus</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphite_anion" title="Phosphite anion">PO<sub>3</sub>H<sup>2−</sup></a></li> <li><a href="/wiki/Phosphite_ester" title="Phosphite ester">P(O–)<sub>3</sub></a></li> <li><a href="/wiki/Phosphoric_acids_and_phosphates" title="Phosphoric acids and phosphates">P<sub>2</sub>O<sub>5</sub>·<span class="texhtml mvar" style="font-style:italic;">n</span>H<sub>2</sub>O</a></li> <li><a href="/wiki/Organophosphate" title="Organophosphate">OP(O–)<sub>3</sub></a></li> <li><a href="/w/index.php?title=Organophosphonic_acid&action=edit&redlink=1" class="new" title="Organophosphonic acid (page does not exist)">–P(OH)<sub>2</sub></a></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">–P(O–)<sub>2</sub></a></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">–P(O)(O–)<sub>2</sub></a></li> <li><a href="/wiki/Phosphinite" title="Phosphinite">–OP<</a> <ul><li>free acid <a href="/wiki/Phosphinous_acids" title="Phosphinous acids">HOP(CF<sub>3</sub>)<sub>2</sub></a></li></ul></li> <li><a href="/wiki/Organophosphinic_acid" title="Organophosphinic acid">HOP(O)<</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">PO<sub>2</sub>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">–P<</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">–P(O)<</a></li> <li><a href="/wiki/Phosphoramidite" title="Phosphoramidite">(–O)<sub>2</sub>PN<</a> <ul><li>e.g. <a href="/wiki/Nucleoside_phosphoramidite" title="Nucleoside phosphoramidite">Nucleoside phosphoramidite</a></li></ul></li> <li><a href="/wiki/Phosphoramidate" title="Phosphoramidate">(–O)<sub>2</sub>P(O)N<</a> <ul><li>e.g. <a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li></ul></li> <li><a href="/w/index.php?title=Phosphorodiamidite&action=edit&redlink=1" class="new" title="Phosphorodiamidite (page does not exist)">–OP(N<)<sub>2</sub></a></li> <li><a href="/wiki/Phosphoramidate" title="Phosphoramidate">–OP(O)(N<)<sub>2</sub></a> <ul><li>e.g. <a href="/wiki/Morpholino" title="Morpholino">Morpholino</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li></ul></li> <li><a href="/wiki/Aminophosphine" title="Aminophosphine">P(N<)<sub>3</sub></a> <ul><li>e.g. <a href="/wiki/Tris(dimethylamino)phosphine" title="Tris(dimethylamino)phosphine">P(NMe<sub>2</sub>)<sub>3</sub></a></li></ul></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">OP(N<)<sub>3</sub></a> <ul><li>e.g. <a href="/wiki/Hexamethylphosphoramide" title="Hexamethylphosphoramide">Hexamethylphosphoramide</a></li> <li><a href="/wiki/Metepa" title="Metepa">Metepa</a></li></ul></li> <li><a href="/w/index.php?title=Phosphorimide_triamide&action=edit&redlink=1" class="new" title="Phosphorimide triamide (page does not exist)">–NP(N<)<sub>3</sub></a></li> <li><a href="/wiki/Phosphonamidate" class="mw-redirect" title="Phosphonamidate">–P(O)(O–)N<</a></li> <li><a href="/w/index.php?title=Phosphonamide&action=edit&redlink=1" class="new" title="Phosphonamide (page does not exist)">–P(O)(N<)<sub>2</sub></a></li> <li><a href="/w/index.php?title=Phosphinamide&action=edit&redlink=1" class="new" title="Phosphinamide (page does not exist)">>P(O)N<</a></li> <li><a href="/wiki/Thiophosphate" title="Thiophosphate">PS<sub><span class="texhtml mvar" style="font-style:italic;">x</span></sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"><span class="texhtml">4-<i>x</i></span></sub></span></span></a></li> <li><a href="/wiki/Organothiophosphate" title="Organothiophosphate">(–O)<sub>3</sub>PS</a></li> <li><a href="/wiki/Cyclophosphines" class="mw-redirect" title="Cyclophosphines">(-P)<sub>5</sub></a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Compounds_of_carbon_with_other_elements_in_the_periodic_table" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:ChemicalBondsToCarbon" title="Template:ChemicalBondsToCarbon"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:ChemicalBondsToCarbon" title="Template talk:ChemicalBondsToCarbon"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:ChemicalBondsToCarbon" title="Special:EditPage/Template:ChemicalBondsToCarbon"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Compounds_of_carbon_with_other_elements_in_the_periodic_table" style="font-size:114%;margin:0 4em">Compounds of <a href="/wiki/Carbon" title="Carbon">carbon</a> with other elements in the periodic table</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd wikitable" style="width:100%;padding:0"><div style="padding:0 0.25em"> <table cellpadding="3" style="margin:0 auto"> <tbody><tr> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">CH</a> </td> <td colspan="1" style="border:none"> </td> <td colspan="11" style="border:none" rowspan="3"> </td> <td colspan="5" style="border:none"> </td> <td style="background-color:#FFE4E1">He </td></tr> <tr> <td style="background-color:#99bbff"><a href="/wiki/Organolithium_reagent" title="Organolithium reagent">CLi</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoberyllium_chemistry" title="Organoberyllium chemistry">CBe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organoboron_chemistry" title="Organoboron chemistry">CB</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">CC</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93nitrogen_bond" title="Carbon–nitrogen bond">CN</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93oxygen_bond" title="Carbon–oxygen bond">CO</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organofluorine_chemistry" title="Organofluorine chemistry">CF</a> </td> <td style="background-color:#FFE4E1">Ne </td></tr> <tr> <td style="background-color:#98FF98"><a href="/wiki/Organosodium_chemistry" title="Organosodium chemistry">CNa</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organomagnesium_chemistry" class="mw-redirect" title="Organomagnesium chemistry">CMg</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoaluminium_chemistry" title="Organoaluminium chemistry">CAl</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organosilicon_chemistry" title="Organosilicon chemistry">CSi</a> </td> <td style="background-color:#99bbff"><a class="mw-selflink selflink">CP</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organosulfur_chemistry" title="Organosulfur chemistry">CS</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organochlorine_chemistry" title="Organochlorine chemistry">CCl</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoargon_chemistry" class="mw-redirect" title="Organoargon chemistry">CAr</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organopotassium_chemistry" class="mw-redirect" title="Organopotassium chemistry">CK</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organocalcium_chemistry" class="mw-redirect" title="Organocalcium chemistry">CCa</a> </td> <td> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoscandium_chemistry" title="Organoscandium chemistry">CSc</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organotitanium_chemistry" title="Organotitanium chemistry">CTi</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organovanadium_chemistry" title="Organovanadium chemistry">CV</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organochromium_chemistry" title="Organochromium chemistry">CCr</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomanganese_chemistry" title="Organomanganese chemistry">CMn</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoiron_chemistry" title="Organoiron chemistry">CFe</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organocobalt_chemistry" title="Organocobalt chemistry">CCo</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organonickel_chemistry" title="Organonickel chemistry">CNi</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organocopper_chemistry" title="Organocopper chemistry">CCu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organozinc_chemistry" title="Organozinc chemistry">CZn</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogallium_chemistry" title="Organogallium chemistry">CGa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogermanium_chemistry" title="Organogermanium chemistry">CGe</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoarsenic_chemistry" title="Organoarsenic chemistry">CAs</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoselenium_chemistry" title="Organoselenium chemistry">CSe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organobromine_chemistry" title="Organobromine chemistry">CBr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organokrypton_chemistry" title="Organokrypton chemistry">CKr</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organorubidium_chemistry" class="mw-redirect" title="Organorubidium chemistry">CRb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organostrontium_chemistry" class="mw-redirect" title="Organostrontium chemistry">CSr</a> </td> <td> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoyttrium_chemistry" title="Organoyttrium chemistry">CY</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organozirconium_chemistry" class="mw-redirect" title="Organozirconium chemistry">CZr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoniobium_chemistry" title="Organoniobium chemistry">CNb</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomolybdenum_chemistry" title="Organomolybdenum chemistry">CMo</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotechnetium_chemistry" title="Organotechnetium chemistry">CTc</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoruthenium_chemistry" title="Organoruthenium chemistry">CRu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organorhodium_chemistry" title="Organorhodium chemistry">CRh</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organopalladium_chemistry" title="Organopalladium chemistry">CPd</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organosilver_chemistry" title="Organosilver chemistry">CAg</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organocadmium_chemistry" title="Organocadmium chemistry">CCd</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoindium_chemistry" title="Organoindium chemistry">CIn</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organotin_chemistry" title="Organotin chemistry">CSn</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoantimony_chemistry" title="Organoantimony chemistry">CSb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotellurium_chemistry" title="Organotellurium chemistry">CTe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organoiodine_chemistry" title="Organoiodine chemistry">CI</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoxenon_chemistry" title="Organoxenon chemistry">CXe</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organocesium_chemistry" class="mw-redirect" title="Organocesium chemistry">CCs</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organobarium_chemistry" class="mw-redirect" title="Organobarium chemistry">CBa</a> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="1 asterisk" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/16px-Asterisks_one.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/24px-Asterisks_one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/32px-Asterisks_one.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CLu</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organohafnium_chemistry" class="mw-redirect" title="Organohafnium chemistry">CHf</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotantalum_chemistry" title="Organotantalum chemistry">CTa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotungsten_chemistry" class="mw-redirect" title="Organotungsten chemistry">CW</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organorhenium_chemistry" title="Organorhenium chemistry">CRe</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoosmium_chemistry" class="mw-redirect" title="Organoosmium chemistry">COs</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoiridium_chemistry" title="Organoiridium chemistry">CIr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoplatinum_chemistry" title="Organoplatinum chemistry">CPt</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogold_chemistry" title="Organogold chemistry">CAu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomercury_chemistry" title="Organomercury chemistry">CHg</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organothallium_chemistry" title="Organothallium chemistry">CTl</a> </td> <td style="background-color:#98FF82"><a href="/wiki/Organolead_chemistry" title="Organolead chemistry">CPb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organobismuth_chemistry" title="Organobismuth chemistry">CBi</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">CPo</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoastatine_chemistry" title="Organoastatine chemistry">CAt</a> </td> <td style="background-color:#FFE4E1">Rn </td></tr> <tr style="background-color:#FFE4E1"> <td style="background-color:#FFE4E1">Fr </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoradium_chemistry" class="mw-redirect" title="Organoradium chemistry">CRa</a> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="2 asterisks" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/16px-Asterisks_two.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/24px-Asterisks_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/32px-Asterisks_two.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Lr</a> </td> <td>Rf </td> <td>Db </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoseaborgium_chemistry" class="mw-redirect" title="Organoseaborgium chemistry">CSg</a> </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="border:none; line-height:0.7em;">  </td></tr> <tr style="background-color:#F0DC82"> <td colspan="2" style="border:none; background-color:white"> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="1 asterisk" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/16px-Asterisks_one.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/24px-Asterisks_one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/32px-Asterisks_one.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CLa</a> </td> <td><a href="/wiki/Organocerium_chemistry" title="Organocerium chemistry">CCe</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CPr</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CNd</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CPm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CSm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CEu</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CGd</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CTb</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CDy</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CHo</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CEr</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CTm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CYb</a> </td></tr> <tr style="background-color:#FFE4E1"> <td colspan="2" style="border:none; background-color:white"> </td> <td style="text-align:center; vertical-align:middle; background:white;"><span class="skin-invert-image" typeof="mw:File"><span><img alt="2 asterisks" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/16px-Asterisks_two.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/24px-Asterisks_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/32px-Asterisks_two.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Ac</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organothorium_chemistry" title="Organothorium chemistry">CTh</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CPa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organouranium_chemistry" title="Organouranium chemistry">CU</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoneptunium_chemistry" title="Organoneptunium chemistry">CNp</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CPu</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CAm</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CCm</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CBk</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CCf</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CEs</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Fm</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Md</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">No</a> </td></tr></tbody></table> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Legend</th><td class="navbox-list-with-group navbox-list navbox-even wikitable" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"><ul><li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonds</a> to carbon</li><li><span style="background:#99bbff; padding:3px;; display:inline-block;">Core organic chemistry</span></li><li><span style="background:#98FF98; padding:3px;; display:inline-block;">Many uses in chemistry</span></li><li><span style="background:#F0DC82; padding:3px;; display:inline-block;">Academic research, no widespread use</span></li><li><span style="background:#FFE4E1; padding:3px;; display:inline-block;">Bond unknown</span></li></ul></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2182492#identifiers" 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