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<span>Scope</span> </div> </a> <ul id="toc-Scope-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Limits" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Limits"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Limits</span> </div> </a> <ul id="toc-Limits-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Photo-Fries_rearrangement" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Photo-Fries_rearrangement"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Photo-Fries rearrangement</span> </div> </a> <ul id="toc-Photo-Fries_rearrangement-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anionic_Fries_rearrangement" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Anionic_Fries_rearrangement"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Anionic Fries rearrangement</span> </div> </a> <ul id="toc-Anionic_Fries_rearrangement-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">6</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">7</span> <span>References</span> </div> </a> <ul id="toc-References-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 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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Fries rearrangement</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 15 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-15" 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">15 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/%D8%A5%D8%B9%D8%A7%D8%AF%D8%A9_%D8%AA%D8%B1%D8%AA%D9%8A%D8%A8_%D9%81%D8%B1%D9%8A%D8%B3" title="إعادة ترتيب فريس – Arabic" lang="ar" hreflang="ar" data-title="إعادة ترتيب فريس" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Transposici%C3%B3_de_Fries" title="Transposició de Fries – Catalan" lang="ca" hreflang="ca" data-title="Transposició de Fries" 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/Fries%C5%AFv_p%C5%99esmyk" title="Friesův přesmyk – Czech" lang="cs" hreflang="cs" data-title="Friesův přesmyk" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Fries-Umlagerung" title="Fries-Umlagerung – German" lang="de" hreflang="de" data-title="Fries-Umlagerung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D8%A7%D8%B2%D8%A2%D8%B1%D8%A7%DB%8C%DB%8C_%D9%81%D8%B1%DB%8C%D8%B3" title="بازآرایی فریس – Persian" lang="fa" hreflang="fa" data-title="بازآرایی فریس" 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/R%C3%A9arrangement_de_Fries" title="Réarrangement de Fries – French" lang="fr" hreflang="fr" data-title="Réarrangement de Fries" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Trasposizione_di_Fries" title="Trasposizione di Fries – Italian" lang="it" hreflang="it" data-title="Trasposizione di Fries" 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/Fries-omlegging" title="Fries-omlegging – Dutch" lang="nl" hreflang="nl" data-title="Fries-omlegging" 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%95%E3%83%AA%E3%83%BC%E3%82%B9%E8%BB%A2%E4%BD%8D" title="フリース転位 – Japanese" lang="ja" hreflang="ja" data-title="フリース転位" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Przegrupowanie_Friesa" title="Przegrupowanie Friesa – Polish" lang="pl" hreflang="pl" data-title="Przegrupowanie Friesa" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Transpozi%C8%9Bie_Fries" title="Transpoziție Fries – Romanian" lang="ro" hreflang="ro" data-title="Transpoziție Fries" 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%9F%D0%B5%D1%80%D0%B5%D0%B3%D1%80%D1%83%D0%BF%D0%BF%D0%B8%D1%80%D0%BE%D0%B2%D0%BA%D0%B0_%D0%A4%D1%80%D0%B8%D1%81%D0%B0" title="Перегруппировка Фриса – Russian" lang="ru" hreflang="ru" data-title="Перегруппировка Фриса" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fries-toisiintuminen" title="Fries-toisiintuminen – Finnish" lang="fi" hreflang="fi" data-title="Fries-toisiintuminen" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%BE%D1%82%D0%BE%D0%BF%D0%B5%D1%80%D0%B5%D0%B3%D1%80%D1%83%D0%BF%D1%83%D0%B2%D0%B0%D0%BD%D0%BD%D1%8F_%D0%A4%D1%80%D1%96%D1%81%D0%B0" title="Фотоперегрупування Фріса – Ukrainian" lang="uk" hreflang="uk" data-title="Фотоперегрупування Фріса" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%BC%97%E8%B5%96%E6%96%AF%E9%87%8D%E6%8E%92%E5%8F%8D%E5%BA%94" title="弗赖斯重排反应 – 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The present address (URL) is a <a href="/wiki/Help:Permanent_link" title="Help:Permanent link">permanent link</a> to this version.</b></p><div id="revision-info-current-plain" style="display: none;">Revision as of 11:41, 26 July 2024 by <a href="/wiki/User:Pygos" class="mw-userlink" title="User:Pygos" data-mw-revid="1236763004"><bdi>Pygos</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Pygos" class="mw-usertoollinks-talk" title="User talk:Pygos">talk</a> | <a href="/wiki/Special:Contributions/Pygos" class="mw-usertoollinks-contribs" title="Special:Contributions/Pygos">contribs</a>)</span> <span class="comment">(added content)</span></div></div><div id="mw-revision-nav">(<a href="/w/index.php?title=Fries_rearrangement&diff=prev&oldid=1236763004" title="Fries rearrangement">diff</a>) <a href="/w/index.php?title=Fries_rearrangement&direction=prev&oldid=1236763004" title="Fries rearrangement">← Previous revision</a> | Latest revision (diff) | Newer revision → (diff)</div></div></div></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Rearrangement reaction of a phenolic ester to a keto-substituted phenol</div> <style data-mw-deduplicate="TemplateStyles:r1049416944">.mw-parser-output .ib-reactionbox{border-collapse:collapse}.mw-parser-output .ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}</style> <table class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Fries rearrangement </th></tr> <tr> <td>Named after </td> <td><a href="/wiki/Karl_Theophil_Fries" title="Karl Theophil Fries">Karl Theophil Fries</a> </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">Rearrangement reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td>Organic Chemistry Portal </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/fries-rearrangement.shtm">fries-rearrangement</a></span> </td></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000444">RXNO:0000444</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Fries rearrangement</b>, named for the German chemist <a href="/wiki/Karl_Theophil_Fries" title="Karl Theophil Fries">Karl Theophil Fries</a>, is a <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reaction</a> of a phenolic ester to a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxy</a> <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> <a href="/wiki/Ketone" title="Ketone">ketone</a> by <a href="/wiki/Catalysis" title="Catalysis">catalysis</a> of <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a>.<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><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-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> </p><p>It involves migration of an <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> group of <a href="/wiki/Phenol" title="Phenol">phenol</a> ester to the <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> ring. The reaction is <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">ortho and para selective</a> and one of the two products can be favoured by changing reaction conditions, such as <a href="/wiki/Temperature" title="Temperature">temperature</a> and <a href="/wiki/Solvent" title="Solvent">solvent</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fries_rearrangement&action=edit&section=1" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Despite many efforts, a definitive <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">reaction mechanism</a> for the Fries rearrangement has not been determined. Evidence for inter- and <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a> mechanisms have been obtained by <a href="/wiki/Crossover_experiment_(chemistry)" title="Crossover experiment (chemistry)">crossover experiments</a> with mixed reactants.<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. (April 2024)">citation needed</span></a></i>]</sup>The reaction progress is not dependent on <a href="/wiki/Solvent" title="Solvent">solvent</a> or <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrate</a>. A widely accepted mechanism involves a <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> intermediate. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Fries_rearrangement.svg" class="mw-file-description" title="The Fries rearrangement"><img alt="The Fries rearrangement" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Fries_rearrangement.svg/600px-Fries_rearrangement.svg.png" decoding="async" width="600" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Fries_rearrangement.svg/900px-Fries_rearrangement.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Fries_rearrangement.svg/1200px-Fries_rearrangement.svg.png 2x" data-file-width="3974" data-file-height="1454" /></a><figcaption>The Fries rearrangement</figcaption></figure> <p>In the first reaction step a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> for instance <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a> <span class="chemf nowrap">AlCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;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">3</sub></span></span></span> co-ordinates to the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> oxygen atom of the <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> group. This oxygen atom is more <a href="/wiki/Electron" title="Electron">electron</a> rich than the <a href="/wiki/Phenol" title="Phenol">phenolic</a> oxygen atom and is the preferred <a href="/wiki/Lewis_base" class="mw-redirect" title="Lewis base">Lewis base</a>. This interaction <a href="/wiki/Chemical_polarity" title="Chemical polarity">polarizes</a> the <a href="/wiki/Covalent_bond" title="Covalent bond">bond</a> between the acyl residue and the phenolic oxygen atom and the aluminium chloride group rearranges to the phenolic oxygen atom. This generates a free <a href="/wiki/Acylium" class="mw-redirect" title="Acylium">acylium</a> <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> which reacts in a classical <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> with the aromatic ring. The abstracted proton is released as <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> where the chlorine is derived from aluminium chloride. The orientation of the substitution reaction is temperature dependent. A low reaction temperature favors <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">para substitution</a> and with high temperatures the <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">ortho</a> product prevails, this can be rationalised as exhibiting classic <a href="/wiki/Thermodynamic_versus_kinetic_reaction_control" title="Thermodynamic versus kinetic reaction control">thermodynamic versus kinetic reaction control</a> as the ortho product can form a more stable bidentate complex with the aluminium.<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> Formation of the ortho product is also favoured in non-polar solvents; as the solvent polarity increases, the ratio of the para product also increases.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Scope">Scope</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fries_rearrangement&action=edit&section=2" title="Edit section: Scope"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Phenol" title="Phenol">Phenols</a> react to form <a href="/wiki/Ester" title="Ester">esters</a> instead of hydroxyarylketones when reacted with <a href="/wiki/Acyl_halide" title="Acyl halide">acyl halides</a> under <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylation</a> conditions. Therefore, this reaction is of industrial importance for the synthesis of hydroxyarylketones, which are important intermediates for several pharmaceuticals. As an alternative to <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a>, other <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a> such as <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> and <a href="/wiki/Bismuth" title="Bismuth">bismuth</a> <a href="/wiki/Triflate" title="Triflate">triflate</a> or strong protic acids such as <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a> and <a href="/wiki/Methanesulfonic_acid" title="Methanesulfonic acid">methanesulfonic acid</a> can also be used. <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. (April 2024)">citation needed</span></a></i>]</sup> In order to avoid the use of these corrosive and environmentally unfriendly <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a> altogether research into alternative <a href="/wiki/Heterogeneous_catalysis" title="Heterogeneous catalysis">heterogeneous</a> catalysts is actively pursued. </p> <div class="mw-heading mw-heading2"><h2 id="Limits">Limits</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fries_rearrangement&action=edit&section=3" title="Edit section: Limits"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In all instances only <a href="/wiki/Ester" title="Ester">esters</a> can be used with stable acyl components that can withstand the harsh conditions of the Fries rearrangement. If the aromatic or the acyl component is heavily substituted then the <a href="/wiki/Chemical_yield" class="mw-redirect" title="Chemical yield">chemical yield</a> will drop due to <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric</a> constraints. Deactivating meta-directing groups on the benzene group will also have an adverse effect as can be expected for a <a href="/wiki/Friedel-Crafts_reaction" class="mw-redirect" title="Friedel-Crafts reaction">Friedel–Crafts acylation</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Photo-Fries_rearrangement">Photo-Fries rearrangement</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fries_rearrangement&action=edit&section=4" title="Edit section: Photo-Fries rearrangement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In addition to the ordinary thermal phenyl ester reaction a <a href="/wiki/Photochemical" class="mw-redirect" title="Photochemical">photochemical</a> variant is possible. The <b>photo-Fries rearrangement</b> can likewise give [1,3] and [1,5] products,<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><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> which involves a <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">reaction mechanism</a>. This reaction is also possible with deactivating <a href="/wiki/Substituent" title="Substituent">substituents</a> on the aromatic group. Because the yields are low this procedure is not used in commercial production. However, photo-Fries rearrangement may occur naturally, for example when a plastic object made of aromatic <a href="/wiki/Polycarbonate" title="Polycarbonate">polycarbonate</a>, <a href="/wiki/Polyester" title="Polyester">polyester</a> or <a href="/wiki/Polyurethane" title="Polyurethane">polyurethane</a>, is exposed to the sun (aliphatic carbonyls undergo <a href="/wiki/Norrish_reaction" title="Norrish reaction">Norrish reactions</a>, which are somewhat similar). In this case, <a href="/wiki/Photodissociation" title="Photodissociation">photolysis</a> of the ester groups would lead to leaching of phthalate from the plastic.<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> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Fries_rearrangement_(photo).svg" class="mw-file-description" title="Photo Fries rearrangement"><img alt="Photo Fries rearrangement" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Fries_rearrangement_%28photo%29.svg/600px-Fries_rearrangement_%28photo%29.svg.png" decoding="async" width="600" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Fries_rearrangement_%28photo%29.svg/900px-Fries_rearrangement_%28photo%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Fries_rearrangement_%28photo%29.svg/1200px-Fries_rearrangement_%28photo%29.svg.png 2x" data-file-width="4549" data-file-height="838" /></a><figcaption>Photo Fries rearrangement</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Anionic_Fries_rearrangement">Anionic Fries rearrangement</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fries_rearrangement&action=edit&section=5" title="Edit section: Anionic Fries rearrangement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the anionic Fries rearrangement <a href="/wiki/Ortho-metalation" class="mw-redirect" title="Ortho-metalation">ortho-metalation</a> of aryl esters, <a href="/wiki/Carbamates" class="mw-redirect" title="Carbamates">carbamates</a> and carbonates with a strong base results in a rearrangement to give ortho-carbonyl species.<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> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Anion_Fries_Rearrangement.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Anion_Fries_Rearrangement.png/220px-Anion_Fries_Rearrangement.png" decoding="async" width="220" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Anion_Fries_Rearrangement.png/330px-Anion_Fries_Rearrangement.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Anion_Fries_Rearrangement.png/440px-Anion_Fries_Rearrangement.png 2x" data-file-width="2041" data-file-height="561" /></a><figcaption>Mechanism of Anion Fries Rearrangement</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=Fries_rearrangement&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Friedel%E2%80%93Crafts_alkylation" class="mw-redirect" title="Friedel–Crafts alkylation">Friedel–Crafts alkylation</a>-like reactions: <ul><li><a href="/wiki/Hofmann%E2%80%93Martius_rearrangement" title="Hofmann–Martius rearrangement">Hofmann–Martius rearrangement</a></li> <li><a href="/wiki/Fischer%E2%80%93Hepp_rearrangement" title="Fischer–Hepp rearrangement">Fischer–Hepp rearrangement</a></li></ul></li> <li><a href="/wiki/Duff_reaction" title="Duff reaction">Duff reaction</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=Fries_rearrangement&action=edit&section=7" 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"><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="CITEREFFries,_K.Finck,_G.1908" class="citation journal cs1"><a href="/wiki/Karl_Theophil_Fries" title="Karl Theophil Fries">Fries, K.</a>; Finck, G. (1908). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1426311">"Über Homologe des Cumaranons und ihre Abkömmlinge"</a>. <i><a href="/wiki/Chemische_Berichte" title="Chemische Berichte">Chemische Berichte</a></i>. <b>41</b> (3): 4271–4284. <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%2Fcber.190804103146">10.1002/cber.190804103146</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemische+Berichte&rft.atitle=%C3%9Cber+Homologe+des+Cumaranons+und+ihre+Abk%C3%B6mmlinge&rft.volume=41&rft.issue=3&rft.pages=4271-4284&rft.date=1908&rft_id=info%3Adoi%2F10.1002%2Fcber.190804103146&rft.au=Fries%2C+K.&rft.au=Finck%2C+G.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1426311&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFries+rearrangement" 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="CITEREFFries,_K.Pfaffendorf,_W.1910" class="citation journal cs1">Fries, K.; Pfaffendorf, W. (1910). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1426389">"Über ein Kondensationsprodukt des Cumaranons und seine Umwandlung in Oxindirubin"</a>. <i><a href="/wiki/Chemische_Berichte" title="Chemische Berichte">Chemische Berichte</a></i>. <b>43</b> (1): 212–219. <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%2Fcber.19100430131">10.1002/cber.19100430131</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemische+Berichte&rft.atitle=%C3%9Cber+ein+Kondensationsprodukt+des+Cumaranons+und+seine+Umwandlung+in+Oxindirubin&rft.volume=43&rft.issue=1&rft.pages=212-219&rft.date=1910&rft_id=info%3Adoi%2F10.1002%2Fcber.19100430131&rft.au=Fries%2C+K.&rft.au=Pfaffendorf%2C+W.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1426389&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFries+rearrangement" 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">March, J. <i>Advanced Organic Chemistry</i>, 3rd Ed.; John Wiley & Sons: Chichester, 1985; S. 499ff.</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">Blatt, A. H. <a href="/wiki/Organic_Reactions" title="Organic Reactions"><i>Org. React.</i></a> <b>1942</b>, <i>1</i>.</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="CITEREFSainsbury1992" class="citation book cs1">Sainsbury, Malcolm (1992). <i>Aromatic Chemistry (Oxford Chemistry Primers)</i>. Oxford University Press. p. 65. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0198556748" title="Special:BookSources/0198556748"><bdi>0198556748</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Aromatic+Chemistry+%28Oxford+Chemistry+Primers%29&rft.pages=65&rft.pub=Oxford+University+Press&rft.date=1992&rft.isbn=0198556748&rft.aulast=Sainsbury&rft.aufirst=Malcolm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFries+rearrangement" class="Z3988"></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="CITEREFKürtiCzakó2005" class="citation book cs1">Kürti, László; Czakó, Barbara (2005). <i>Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms</i>. 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(the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/P04614.html">photo-Fries rearrangement</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.P04614">10.1351/goldbook.P04614</a></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="CITEREFBelluš2007" class="citation journal cs1">Belluš, Daniel (5 January 2007). 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"Environmental Effects on Polymeric Materials". <i>Plastics and the Environment</i>. <b>8</b>: 311–358. <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%2F0471721557.ch8">10.1002/0471721557.ch8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471721550" title="Special:BookSources/9780471721550"><bdi>9780471721550</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Plastics+and+the+Environment&rft.atitle=Environmental+Effects+on+Polymeric+Materials&rft.volume=8&rft.pages=311-358&rft.date=2004-11-07&rft_id=info%3Adoi%2F10.1002%2F0471721557.ch8&rft.isbn=9780471721550&rft.aulast=Searle&rft.aufirst=Norma+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFries+rearrangement" 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="CITEREFKorbLang2019" class="citation journal cs1">Korb, Marcus; Lang, Heinrich (2019). "The anionic Fries rearrangement: a convenient route to ortho-functionalized aromatics". <i>Chemical Society Reviews</i>. <b>48</b> (10): 2829–2882. <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%2FC8CS00830B">10.1039/C8CS00830B</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/31066387">31066387</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:206131063">206131063</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Society+Reviews&rft.atitle=The+anionic+Fries+rearrangement%3A+a+convenient+route+to+ortho-functionalized+aromatics&rft.volume=48&rft.issue=10&rft.pages=2829-2882&rft.date=2019&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A206131063%23id-name%3DS2CID&rft_id=info%3Apmid%2F31066387&rft_id=info%3Adoi%2F10.1039%2FC8CS00830B&rft.aulast=Korb&rft.aufirst=Marcus&rft.au=Lang%2C+Heinrich&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFries+rearrangement" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Fries_rearrangement&oldid=1236763004">https://en.wikipedia.org/w/index.php?title=Fries_rearrangement&oldid=1236763004</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Rearrangement_reactions" title="Category:Rearrangement reactions">Rearrangement reactions</a></li><li><a href="/wiki/Category:Name_reactions" title="Category:Name reactions">Name reactions</a></li><li><a href="/wiki/Category:Free_radical_reactions" title="Category:Free radical reactions">Free radical reactions</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_April_2024" title="Category:Articles with unsourced statements from April 2024">Articles with unsourced statements from April 2024</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 26 July 2024, at 11:41<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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