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mw-first-heading"><span class="mw-page-title-main">Ritter reaction</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. 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href="https://cs.wikipedia.org/wiki/Ritterova_reakce" title="Ritterova reakce – Czech" lang="cs" hreflang="cs" data-title="Ritterova reakce" 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/Ritter-Reaktion" title="Ritter-Reaktion – German" lang="de" hreflang="de" data-title="Ritter-Reaktion" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Reacci%C3%B3n_de_Ritter" title="Reacción de Ritter – Spanish" lang="es" hreflang="es" data-title="Reacción de Ritter" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%D8%A7%DA%A9%D9%86%D8%B4_%D8%B1%DB%8C%D8%AA%D8%B1" title="واکنش ریتر – Persian" lang="fa" hreflang="fa" data-title="واکنش ریتر" 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%A9action_de_Ritter" title="Réaction de Ritter – French" lang="fr" hreflang="fr" data-title="Réaction de Ritter" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A6%AC%ED%84%B0_%EB%B0%98%EC%9D%91" title="리터 반응 – Korean" lang="ko" hreflang="ko" data-title="리터 반응" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ritter-reactie" title="Ritter-reactie – Dutch" lang="nl" hreflang="nl" data-title="Ritter-reactie" 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%AA%E3%83%83%E3%82%BF%E3%83%BC%E5%8F%8D%E5%BF%9C" title="リッター反応 – Japanese" lang="ja" hreflang="ja" data-title="リッター反応" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Rea%C3%A7%C3%A3o_de_Ritter" title="Reação de Ritter – Portuguese" lang="pt" hreflang="pt" data-title="Reação de Ritter" 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/Reac%C8%9Bie_Ritter" title="Reacție Ritter – Romanian" lang="ro" hreflang="ro" data-title="Reacție Ritter" 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%A0%D0%B5%D0%B0%D0%BA%D1%86%D0%B8%D1%8F_%D0%A0%D0%B8%D1%82%D1%82%D0%B5%D1%80%D0%B0" title="Реакция Риттера – Russian" lang="ru" hreflang="ru" data-title="Реакция Риттера" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A0%D0%B5%D0%B0%D0%BA%D1%86%D1%96%D1%8F_%D0%A0%D1%96%D1%82%D1%82%D0%B5%D1%80%D0%B0" title="Реакція Ріттера – Ukrainian" lang="uk" hreflang="uk" data-title="Реакція Ріттера" 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/%E9%87%8C%E7%89%B9%E5%8F%8D%E5%BA%94" title="里特反应 – Chinese" lang="zh" hreflang="zh" data-title="里特反应" 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/Q902273#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" 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30%; background: #ACE1AF; text-align: center;" colspan="2">Ritter reaction </th></tr> <tr> <td>Named after </td> <td>John J. Ritter </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Addition_reaction" title="Addition reaction">Addition 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/ritter-reaction.shtm">ritter-reaction</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_0000058">RXNO:0000058</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Ritter reaction</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> that transforms a <a href="/wiki/Nitrile" title="Nitrile">nitrile</a> into an <i>N</i>-alkyl <a href="/wiki/Amide" title="Amide">amide</a> using various <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> <a href="/wiki/Alkylating" class="mw-redirect" title="Alkylating">alkylating</a> reagents. The original reaction formed the <a href="/wiki/Alkylation" title="Alkylation">alkylating agent</a> using an <a href="/wiki/Alkene" title="Alkene">alkene</a> in the presence of a <a href="/wiki/Strong_acid" class="mw-redirect" title="Strong acid">strong acid</a>.<sup id="cite_ref-OrgReact17_1-0" class="reference"><a href="#cite_note-OrgReact17-1"><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-Trost_4-0" class="reference"><a href="#cite_note-Trost-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ritter-Reaktion_1d.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Ritter-Reaktion_1d.svg/495px-Ritter-Reaktion_1d.svg.png" decoding="async" width="495" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Ritter-Reaktion_1d.svg/743px-Ritter-Reaktion_1d.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Ritter-Reaktion_1d.svg/990px-Ritter-Reaktion_1d.svg.png 2x" data-file-width="495" data-file-height="100" /></a><figcaption></figcaption></figure> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Mechanism_and_scope">Mechanism and scope</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ritter_reaction&action=edit&section=1" title="Edit section: Mechanism and scope"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Ritter reaction proceeds by the <a href="/wiki/Electrophilic_addition" title="Electrophilic addition">electrophilic addition</a> of either a <a href="/wiki/Carbenium_ion" title="Carbenium ion">carbenium ion</a> or covalent species<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><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> to the <a href="/wiki/Nitrile" title="Nitrile">nitrile</a>. The resulting <a href="/wiki/Nitrilium_ion" class="mw-redirect" title="Nitrilium ion">nitrilium ion</a> is <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> to the desired amide. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ritter_reaction_mechanism,_step_by_step..jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/3/30/Ritter_reaction_mechanism%2C_step_by_step..jpg" decoding="async" width="734" height="217" class="mw-file-element" data-file-width="734" data-file-height="217" /></a><figcaption></figcaption></figure> <p>Primary,<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> secondary,<sup id="cite_ref-Trost_4-1" class="reference"><a href="#cite_note-Trost-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> tertiary,<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> and benzylic<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> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>,<sup id="cite_ref-OrgReact17_1-1" class="reference"><a href="#cite_note-OrgReact17-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> as well as <i>tert</i>-butyl acetate,<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> also successfully react with nitriles in the presence of strong acids to form amides via the Ritter reaction. A wide range of nitriles can be used. In particular, formonitrile (hydrogen cyanide) can be used to prepare formamides, which are useful precursors to isocyanides. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ritter_reaction&action=edit&section=2" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The large scale application of the Ritter reaction is in the synthesis of <a href="/w/index.php?title=Tert-octylamine&action=edit&redlink=1" class="new" title="Tert-octylamine (page does not exist)">tert-octylamine</a>. An estimated 10,000 tons/y (year: 2000) of this and related lipophilic amines are prepared in this way.<sup id="cite_ref-Ullmann_11-0" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Otherwise, the Ritter reaction is most useful in the formation of amines and <a href="/wiki/Amides" class="mw-redirect" title="Amides">amides</a> of pharmaceutical interest. Real world applications include <a href="/wiki/Merck_%26_Co." title="Merck & Co.">Merck</a>'s industrial-scale synthesis of anti-<a href="/wiki/HIV" title="HIV">HIV</a> drug <a href="/wiki/Crixivan" class="mw-redirect" title="Crixivan">Crixivan</a> (indinavir);<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> the production of the falcipain-2 inhibitor <a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a>; the synthesis of the <a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a> aristotelone;<sup id="cite_ref-Kurti_13-0" class="reference"><a href="#cite_note-Kurti-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> and synthesis of <a href="/wiki/Amantadine" title="Amantadine">Amantadine</a>, an antiviral and antiparkinsonian drug.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Other applications of the Ritter reaction include synthesis of <a href="/wiki/Dopamine_receptor" title="Dopamine receptor">dopamine receptor</a> <a href="/wiki/Ligands" class="mw-redirect" title="Ligands">ligands</a><sup id="cite_ref-Kurti_13-1" class="reference"><a href="#cite_note-Kurti-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> and production of racemic <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a> from <a href="/wiki/Allylbenzene" title="Allylbenzene">allylbenzene</a> and <a href="/wiki/Methyl_cyanide" class="mw-redirect" title="Methyl cyanide">methyl cyanide</a>.<sup id="cite_ref-OrgReact17_1-2" class="reference"><a href="#cite_note-OrgReact17-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The Ritter reaction is inferior to most <a href="/wiki/Amination" title="Amination">amination</a> methods because it cogenerates substantial amounts of salts. Illustrative is the conversion of isobutylene to <a href="/wiki/Tert-butylamine" class="mw-redirect" title="Tert-butylamine">tert-butylamine</a> using HCN and <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> followed by base neutralization. The weight of the salt byproduct is greater than the weight of the amine.<sup id="cite_ref-Ullmann_11-1" class="reference"><a href="#cite_note-Ullmann-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In the laboratory, the Ritter reaction suffers from the necessity of an extremely strong acid <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>. Other methods have been proposed in order to promote <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> formation, including photocatalytic <a href="/wiki/Electron_transfer" title="Electron transfer">electron transfer</a><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> or direct <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">photolysis</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ritter_reaction&action=edit&section=3" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The reaction is named after John J. Ritter, who supervised the Ph.D. thesis work of <a href="/w/index.php?title=P._Paul_Minieri&action=edit&redlink=1" class="new" title="P. Paul Minieri (page does not exist)">P. Paul Minieri</a>. </p> <ul><li><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="CITEREFRitterMinieri1948" class="citation journal cs1">Ritter, John J.; Minieri, P. Paul (1948). "A New Reaction of Nitriles. I. Amides from Alkenes and Mononitriles". <i>Journal of the American Chemical Society</i>. <b>70</b> (12): 4045–8. <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%2Fja01192a022">10.1021/ja01192a022</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/18105932">18105932</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=A+New+Reaction+of+Nitriles.+I.+Amides+from+Alkenes+and+Mononitriles&rft.volume=70&rft.issue=12&rft.pages=4045-8&rft.date=1948&rft_id=info%3Adoi%2F10.1021%2Fja01192a022&rft_id=info%3Apmid%2F18105932&rft.aulast=Ritter&rft.aufirst=John+J.&rft.au=Minieri%2C+P.+Paul&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRitterKalish1948" class="citation journal cs1">Ritter, John J.; Kalish, Joseph (1948). "A New Reaction of Nitriles. II. Synthesis of <i>t</i>-Carbinamines". <i>Journal of the American Chemical Society</i>. <b>70</b> (12): 4048–50. <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%2Fja01192a023">10.1021/ja01192a023</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/18105933">18105933</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=A+New+Reaction+of+Nitriles.+II.+Synthesis+of+t-Carbinamines&rft.volume=70&rft.issue=12&rft.pages=4048-50&rft.date=1948&rft_id=info%3Adoi%2F10.1021%2Fja01192a023&rft_id=info%3Apmid%2F18105933&rft.aulast=Ritter&rft.aufirst=John+J.&rft.au=Kalish%2C+Joseph&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZil'berman1960" class="citation journal cs1">Zil'berman, E. N. (1960). "Some reactions of nitriles with the formation of a new nitrogen–carbon bond". <i>Russian Chemical Reviews</i>. <b>29</b> (6): 331–340. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1960RuCRv..29..331Z">1960RuCRv..29..331Z</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1070%2FRC1960v029n06ABEH001235">10.1070/RC1960v029n06ABEH001235</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:250896801">250896801</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Russian+Chemical+Reviews&rft.atitle=Some+reactions+of+nitriles+with+the+formation+of+a+new+nitrogen%E2%80%93carbon+bond&rft.volume=29&rft.issue=6&rft.pages=331-340&rft.date=1960&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A250896801%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1070%2FRC1960v029n06ABEH001235&rft_id=info%3Abibcode%2F1960RuCRv..29..331Z&rft.aulast=Zil%27berman&rft.aufirst=E.+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" class="Z3988"></span></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=Ritter_reaction&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-OrgReact17-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-OrgReact17_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-OrgReact17_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-OrgReact17_1-2"><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="CITEREFKrimenCota1969" class="citation book cs1">Krimen, L.I.; Cota, Donald J. (1969). Adams, Rodger (ed.). <i>Organic Reaction Volume 17</i>. London: John Wiley & Sons, Inc. pp. 213–326. <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%2F0471264180.or017.03">10.1002/0471264180.or017.03</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471196150" title="Special:BookSources/9780471196150"><bdi>9780471196150</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Reaction+Volume+17&rft.place=London&rft.pages=213-326&rft.pub=John+Wiley+%26+Sons%2C+Inc&rft.date=1969&rft_id=info%3Adoi%2F10.1002%2F0471264180.or017.03&rft.isbn=9780471196150&rft.aulast=Krimen&rft.aufirst=L.I.&rft.au=Cota%2C+Donald+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" 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="CITEREFJohnsonMadroñero1966" class="citation book cs1">Johnson, Francis; Madroñero, Ramón (1966). "Heterocyclic Syntheses Involving Nitrilium Salts and Nitriles under Acidic Conditions". <i>Advances in Heterocyclic Chemistry Volume 6</i>. Vol. 6. pp. 95–146. <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%2FS0065-2725%2808%2960576-0">10.1016/S0065-2725(08)60576-0</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780120206063" title="Special:BookSources/9780120206063"><bdi>9780120206063</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Heterocyclic+Syntheses+Involving+Nitrilium+Salts+and+Nitriles+under+Acidic+Conditions&rft.btitle=Advances+in+Heterocyclic+Chemistry+Volume+6&rft.pages=95-146&rft.date=1966&rft_id=info%3Adoi%2F10.1016%2FS0065-2725%2808%2960576-0&rft.isbn=9780120206063&rft.aulast=Johnson&rft.aufirst=Francis&rft.au=Madro%C3%B1ero%2C+Ram%C3%B3n&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRappoportMeyersSircar1970" class="citation book cs1">Rappoport, Zvi; Meyers, A. I.; Sircar, J. C. (1970). <i>The Cyano Group</i> (1st ed.). Charlottesville, VA: Wiley Interscience. pp. 341–421. <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%2F9780470771242.ch8">10.1002/9780470771242.ch8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471709138" title="Special:BookSources/9780471709138"><bdi>9780471709138</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Cyano+Group&rft.place=Charlottesville%2C+VA&rft.pages=341-421&rft.edition=1st&rft.pub=Wiley+Interscience&rft.date=1970&rft_id=info%3Adoi%2F10.1002%2F9780470771242.ch8&rft.isbn=9780471709138&rft.aulast=Rappoport&rft.aufirst=Zvi&rft.au=Meyers%2C+A.+I.&rft.au=Sircar%2C+J.+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" class="Z3988"></span></span> </li> <li id="cite_note-Trost-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Trost_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Trost_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBishop1991" class="citation book cs1">Bishop, Roger (1991). "Section 1.9 – Ritter-type Reactions". <i>Comprehensive Organic Synthesis Volume 6: Heteroatom Manipulation</i>. pp. 261–300. <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%2FB978-0-08-052349-1.00159-1">10.1016/B978-0-08-052349-1.00159-1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780080359298" title="Special:BookSources/9780080359298"><bdi>9780080359298</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Section+1.9+%E2%80%93+Ritter-type+Reactions&rft.btitle=Comprehensive+Organic+Synthesis+Volume+6%3A+Heteroatom+Manipulation&rft.pages=261-300&rft.date=1991&rft_id=info%3Adoi%2F10.1016%2FB978-0-08-052349-1.00159-1&rft.isbn=9780080359298&rft.aulast=Bishop&rft.aufirst=Roger&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" class="Z3988"></span> <span class="cs1-visible-error citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: </span><span class="cs1-visible-error citation-comment"><code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>)</span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoothJiboduProença1983" class="citation journal cs1">Booth, Brian L.; Jibodu, Kehinde O.; Proença, M. Fernanda J. R. P. (1983). "The chemistry of nitrilium salts. Part 2. The preparation of nitrilium trifluoromethanesulphonate salts and their reactions with some oxygen and sulphur nucleophiles". <i>Journal of the Chemical Society, Perkin Transactions 1</i>: 1067–1073. <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%2FP19830001067">10.1039/P19830001067</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+Chemical+Society%2C+Perkin+Transactions+1&rft.atitle=The+chemistry+of+nitrilium+salts.+Part+2.+The+preparation+of+nitrilium+trifluoromethanesulphonate+salts+and+their+reactions+with+some+oxygen+and+sulphur+nucleophiles&rft.pages=1067-1073&rft.date=1983&rft_id=info%3Adoi%2F10.1039%2FP19830001067&rft.aulast=Booth&rft.aufirst=Brian+L.&rft.au=Jibodu%2C+Kehinde+O.&rft.au=Proen%C3%A7a%2C+M.+Fernanda+J.+R.+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARitter+reaction" 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="CITEREFGarcía_Martínez1989" class="citation journal cs1">García Martínez, A. (1989). 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