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href="#Synthesis_of_cyclopropene_and_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Synthesis of cyclopropene and derivatives</span> </div> </a> <button aria-controls="toc-Synthesis_of_cyclopropene_and_derivatives-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Synthesis of cyclopropene and derivatives subsection</span> </button> <ul id="toc-Synthesis_of_cyclopropene_and_derivatives-sublist" class="vector-toc-list"> <li id="toc-Early_syntheses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Early_syntheses"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Early syntheses</span> </div> </a> <ul id="toc-Early_syntheses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Modern_syntheses_from_allyl_chlorides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Modern_syntheses_from_allyl_chlorides"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Modern syntheses from allyl chlorides</span> </div> </a> <ul id="toc-Modern_syntheses_from_allyl_chlorides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Syntheses_of_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Syntheses_of_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Syntheses of derivatives</span> </div> </a> <ul id="toc-Syntheses_of_derivatives-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions_of_cyclopropene" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions_of_cyclopropene"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions of cyclopropene</span> </div> </a> <ul id="toc-Reactions_of_cyclopropene-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Related_compounds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Related_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Related compounds</span> </div> </a> <ul id="toc-Related_compounds-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 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Available in 28 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-28" 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">28 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%AD%D9%84%D9%82%D9%8A_%D8%A7%D9%84%D8%A8%D8%B1%D9%88%D8%A8%D9%8A%D9%86" title="حلقي البروبين – Arabic" lang="ar" hreflang="ar" data-title="حلقي البروبين" 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/Cicloprop%C3%A8" title="Ciclopropè – Catalan" lang="ca" hreflang="ca" data-title="Ciclopropè" 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/Cyklopropen" title="Cyklopropen – Czech" lang="cs" hreflang="cs" data-title="Cyklopropen" 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/Cyclopropen" title="Cyclopropen – German" lang="de" hreflang="de" data-title="Cyclopropen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CF%85%CE%BA%CE%BB%CE%BF%CF%80%CF%81%CE%BF%CF%80%CE%AD%CE%BD%CE%B9%CE%BF" title="Κυκλοπροπένιο – Greek" lang="el" hreflang="el" data-title="Κυκλοπροπένιο" 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/Ciclopropeno" title="Ciclopropeno – Spanish" lang="es" hreflang="es" data-title="Ciclopropeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Ciklopropeno" title="Ciklopropeno – Esperanto" lang="eo" hreflang="eo" data-title="Ciklopropeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Ziklopropeno" title="Ziklopropeno – Basque" lang="eu" hreflang="eu" data-title="Ziklopropeno" 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%B3%DB%8C%DA%A9%D9%84%D9%88%D9%BE%D8%B1%D9%88%D9%BE%D9%86" title="سیکلوپروپن – Persian" lang="fa" hreflang="fa" data-title="سیکلوپروپن" 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/Cycloprop%C3%A8ne" title="Cyclopropène – French" lang="fr" hreflang="fr" data-title="Cyclopropène" 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/%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A1%9C%ED%94%84%EB%A1%9C%ED%8E%9C" title="사이클로프로펜 – Korean" lang="ko" hreflang="ko" data-title="사이클로프로펜" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ciclopropene" title="Ciclopropene – Italian" lang="it" hreflang="it" data-title="Ciclopropene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Cikloprop%C3%A9n" title="Ciklopropén – Hungarian" lang="hu" hreflang="hu" data-title="Ciklopropén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D1%80%D0%BE%D0%BF%D0%B5%D0%BD" title="Циклопропен – Macedonian" lang="mk" hreflang="mk" data-title="Циклопропен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Siklopropena" title="Siklopropena – Malay" lang="ms" hreflang="ms" data-title="Siklopropena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyclopropeen" title="Cyclopropeen – Dutch" lang="nl" hreflang="nl" data-title="Cyclopropeen" 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%82%B7%E3%82%AF%E3%83%AD%E3%83%97%E3%83%AD%E3%83%9A%E3%83%B3" title="シクロプロペン – Japanese" lang="ja" hreflang="ja" data-title="シクロプロペン" 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/Cyklopropen" title="Cyklopropen – Polish" lang="pl" hreflang="pl" data-title="Cyklopropen" 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/Ciclopropeno" title="Ciclopropeno – Portuguese" lang="pt" hreflang="pt" data-title="Ciclopropeno" 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/Ciclopropen%C4%83" title="Ciclopropenă – Romanian" lang="ro" hreflang="ro" data-title="Ciclopropenă" 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%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D1%80%D0%BE%D0%BF%D0%B5%D0%BD" title="Циклопропен – Russian" lang="ru" hreflang="ru" data-title="Циклопропен" 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/Ciklopropen" title="Ciklopropen – Serbian" lang="sr" hreflang="sr" data-title="Ciklopropen" 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/Ciklopropen" title="Ciklopropen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ciklopropen" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Cyklopropen" title="Cyklopropen – Swedish" lang="sv" hreflang="sv" data-title="Cyklopropen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B5%E0%AE%B3%E0%AF%88%E0%AE%AF%E0%AE%AA%E0%AF%81%E0%AE%B0%E0%AF%8B%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AF%8D" title="வளையபுரோப்பீன் – Tamil" lang="ta" hreflang="ta" data-title="வளையபுரோப்பீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%8B%E0%B9%82%E0%B8%84%E0%B8%A5%E0%B9%82%E0%B8%9E%E0%B8%A3%E0%B8%9E%E0%B8%B5%E0%B8%99" title="ไซโคลโพรพีน – Thai" lang="th" hreflang="th" data-title="ไซโคลโพรพีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%8E%AF%E4%B8%99%E7%83%AF" title="环丙烯 – Wu" lang="wuu" hreflang="wuu" data-title="环丙烯" data-language-autonym="吴语" 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<caption>Cyclopropene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Cyclopropene_2D_skeletal.svg" class="mw-file-description" title="Skeletal formula of cyclopropene"><img alt="Skeletal formula of cyclopropene" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclopropene_2D_skeletal.svg/100px-Cyclopropene_2D_skeletal.svg.png" decoding="async" width="100" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclopropene_2D_skeletal.svg/150px-Cyclopropene_2D_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclopropene_2D_skeletal.svg/200px-Cyclopropene_2D_skeletal.svg.png 2x" data-file-width="529" data-file-height="471" /></a></span> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyclopropene.png" class="mw-file-description" title="Skeletal formula of cyclopropene with implicit hydrogens shown"><img alt="Skeletal formula of cyclopropene with implicit hydrogens shown" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Cyclopropene.png/110px-Cyclopropene.png" decoding="async" width="110" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Cyclopropene.png/165px-Cyclopropene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Cyclopropene.png/220px-Cyclopropene.png 2x" data-file-width="1398" data-file-height="864" /></a><figcaption>Skeletal formula of cyclopropene with implicit hydrogens shown</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cyclopropene-3D-balls.png" class="mw-file-description" title="Ball and stick model of cyclopropene"><img alt="Ball and stick model of cyclopropene" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cyclopropene-3D-balls.png/110px-Cyclopropene-3D-balls.png" decoding="async" width="110" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cyclopropene-3D-balls.png/165px-Cyclopropene-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/Cyclopropene-3D-balls.png/220px-Cyclopropene-3D-balls.png 2x" data-file-width="1100" data-file-height="1006" /></a><figcaption>Ball and stick model of cyclopropene</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Cyclopropene<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></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=2781-85-3">2781-85-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1C%3DC1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.109788.html">109788</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=cyclopropene">cyclopropene</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/123173">123173</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/7B8994OHJ0">7B8994OHJ0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID20893759">DTXSID20893759</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414101#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H4/c1-2-3-1/h1-2H,3H2<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OOXWYYGXTJLWHA-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1C=C1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001400650000000000♠"></span>40.065</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>−36 °C (−33 °F; 237 K) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>51.9-53.9 J K<sup>−1</sup> mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>-2032--2026 kJ mol<sup>−1</sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=442026875&page2=Cyclopropene">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Cyclopropene</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">4</sub></span>. It is the simplest <a href="/wiki/Cycloalkene" title="Cycloalkene">cycloalkene</a>. Because the ring is highly <a href="/wiki/Ring_strain" title="Ring strain">strained</a>, cyclopropene is difficult to prepare and highly reactive. This colorless gas has been the subject for many fundamental studies of bonding and reactivity.<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> It does not occur naturally, but derivatives are known in some <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>. Derivatives of cyclopropene are used commercially to control ripening of some fruit. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=1" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The molecule has a <a href="/wiki/Triangular" class="mw-redirect" title="Triangular">triangular</a> structure. The reduced length of the <a href="/wiki/Alkene" title="Alkene">double bond</a> compared to a <a href="/wiki/Alkane" title="Alkane">single bond</a> causes the angle opposite the double bond to narrow to about 51° from the 60° angle found in <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a>.<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> As with cyclopropane, the carbon–carbon bonding in the ring has increased <a href="/wiki/Atomic_orbital" title="Atomic orbital">p character</a>: the alkene carbon atoms use sp<sup>2.68</sup> <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">hybridization</a> for the ring.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_of_cyclopropene_and_derivatives">Synthesis of cyclopropene and derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=2" title="Edit section: Synthesis of cyclopropene and derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Early_syntheses">Early syntheses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=3" title="Edit section: Early syntheses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first confirmed synthesis of cyclopropene, carried out by Dem'yanov and Doyarenko, involved the <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal decomposition</a> of trimethylcyclopropylammonium hydroxide over platinized clay at approximately 300 °C. <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> This reaction produces mainly <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a> and dimethylcyclopropyl amine, together with about 5% of cyclopropene. Later Schlatter improved the pyrolytic reaction conditions using platinized <a href="/wiki/Asbestos" title="Asbestos">asbestos</a> as a <a href="/wiki/Catalysis" title="Catalysis">catalyst</a> at 320–330 °C and obtained cyclopropene in 45% <a href="/wiki/Yield_(chemistry)" title="Yield (chemistry)">yield</a>.<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><p>Cyclopropene can also be obtained in about 1% yield by thermolysis of the adduct of <a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">cycloheptatriene</a> and <a href="/wiki/Dimethyl_acetylenedicarboxylate" title="Dimethyl acetylenedicarboxylate">dimethyl acetylenedicarboxylate</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Modern_syntheses_from_allyl_chlorides">Modern syntheses from allyl chlorides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=4" title="Edit section: Modern syntheses from allyl chlorides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Allyl_chloride" title="Allyl chloride">Allyl chloride</a> undergoes <a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> upon treatment with the base <a href="/wiki/Sodium_amide" title="Sodium amide">sodium amide</a> at 80 °C to produce cyclopropene in about 10% yield.<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> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {CH2=CHCH2Cl + NaNH2}}\longrightarrow {\underset {{\text{cyclo-}} \atop {\text{propene}}}{{\ce {C3H4}}}}+{\ce {NaCl + NH3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CHCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>Cl</mtext> <mo>+</mo> <msubsup> <mtext>NaNH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>cyclo-</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>propene</mtext> </mrow> </mfrac> </munder> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>NaCl</mtext> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {CH2=CHCH2Cl + NaNH2}}\longrightarrow {\underset {{\text{cyclo-}} \atop {\text{propene}}}{{\ce {C3H4}}}}+{\ce {NaCl + NH3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/ee9f6bb2925010b426827607a417d32c043771c1" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -4.171ex; width:52.869ex; height:6.009ex;" alt="{\displaystyle {\ce {CH2=CHCH2Cl + NaNH2}}\longrightarrow {\underset {{\text{cyclo-}} \atop {\text{propene}}}{{\ce {C3H4}}}}+{\ce {NaCl + NH3}}}"></span></dd></dl> <p>The major byproduct of the reaction is <a href="/wiki/Allylamine" title="Allylamine">allylamine</a>. Adding allyl chloride to <a href="/wiki/Sodium_bis(trimethylsilyl)amide" title="Sodium bis(trimethylsilyl)amide">sodium bis(trimethylsilyl)amide</a> in boiling <a href="/wiki/Toluene" title="Toluene">toluene</a> over a period of 45–60 minutes produces the targeted compound in about 40% yield with an improvement in purity:<sup id="cite_ref-Binger_9-0" class="reference"><a href="#cite_note-Binger-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {CH2=CHCH2Cl + NaN(TMS)2}}\longrightarrow {\underset {{\text{cyclo-}} \atop {\text{propene}}}{{\ce {C3H4}}}}+{\ce {NaCl + NH(TMS)2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CHCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>Cl</mtext> <mo>+</mo> <mtext>NaN</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>TMS</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>cyclo-</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>propene</mtext> </mrow> </mfrac> </munder> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>NaCl</mtext> <mo>+</mo> <mtext>NH</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>TMS</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {CH2=CHCH2Cl + NaN(TMS)2}}\longrightarrow {\underset {{\text{cyclo-}} \atop {\text{propene}}}{{\ce {C3H4}}}}+{\ce {NaCl + NH(TMS)2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/738e71e0428abbb6e7886cb5786f1e93c1d5d07e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -4.171ex; width:64.947ex; height:6.176ex;" alt="{\displaystyle {\ce {CH2=CHCH2Cl + NaN(TMS)2}}\longrightarrow {\underset {{\text{cyclo-}} \atop {\text{propene}}}{{\ce {C3H4}}}}+{\ce {NaCl + NH(TMS)2}}}"></span></dd></dl> <p>1-Methylcyclopropene is synthesized similarly but at room temperature from methallylchloride using <a href="/wiki/Phenyllithium" title="Phenyllithium">phenyllithium</a> as the base:<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> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {CH2=C(CH3)CH2Cl + LiC6H5}}\longrightarrow {\underset {{\text{1-methyl-}} \atop {\text{cyclopropene}}}{{\ce {CH3C3H3}}}}+{\ce {LiCl + C6H6}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>Cl</mtext> <mo>+</mo> <msubsup> <mtext>LiC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>1-methyl-</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>cyclopropene</mtext> </mrow> </mfrac> </munder> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>LiCl</mtext> <mo>+</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {CH2=C(CH3)CH2Cl + LiC6H5}}\longrightarrow {\underset {{\text{1-methyl-}} \atop {\text{cyclopropene}}}{{\ce {CH3C3H3}}}}+{\ce {LiCl + C6H6}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5341eb5e8af5fb11e8b7c0dc47d97c93f90d739b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -4.505ex; width:62.252ex; height:6.509ex;" alt="{\displaystyle {\ce {CH2=C(CH3)CH2Cl + LiC6H5}}\longrightarrow {\underset {{\text{1-methyl-}} \atop {\text{cyclopropene}}}{{\ce {CH3C3H3}}}}+{\ce {LiCl + C6H6}}}"></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Syntheses_of_derivatives">Syntheses of derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=5" title="Edit section: Syntheses of derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Treatment of nitrocyclopropanes with <a href="/wiki/Sodium_methoxide" title="Sodium methoxide">sodium methoxide</a> eliminates the nitrite, giving the respective cyclopropene derivative. The synthesis of purely aliphatic cyclopropenes was first illustrated by the copper-catalyzed additions of carbenes to alkynes. In the presence of a copper catalyst, <a href="/wiki/Ethyl_diazoacetate" title="Ethyl diazoacetate">ethyl diazoacetate</a> reacts with acetylenes to give cyclopropenes. 1,2-Dimethylcyclopropene-3-carboxylate arises via this method from <a href="/wiki/2-butyne" class="mw-redirect" title="2-butyne">2-butyne</a>. Copper, as copper sulfate and copper dust, are among the more popular forms of copper used to promote such reactions. <a href="/wiki/Rhodium_acetate" class="mw-redirect" title="Rhodium acetate">Rhodium acetate</a> has also been used. </p> <div class="mw-heading mw-heading2"><h2 id="Reactions_of_cyclopropene">Reactions of cyclopropene</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=6" title="Edit section: Reactions of cyclopropene"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies on cyclopropene mainly focus on the consequences of its high ring strain. At 425 °C, cyclopropene isomerizes to <a href="/wiki/Methylacetylene" class="mw-redirect" title="Methylacetylene">methylacetylene</a> (propyne). </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {C3H4 -> H3CC#CH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <mtext>CH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C3H4 -> H3CC#CH}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/08f942d0488d3ee755f945438c3ff02434164e61" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:22.008ex; height:2.843ex;" alt="{\displaystyle {\ce {C3H4 -> H3CC#CH}}}"></span></dd></dl> <p>Attempted fractional distillation of cyclopropene at –36 °C (its predicted boiling point) results in polymerization. The mechanism is assumed to be a free-radical chain reaction, and the product, based on NMR spectra, is thought to be polycyclopropane. </p><p>Cyclopropene undergoes the <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a> with <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> to give endo-tricyclo[3.2.1.0<sup>2,4</sup>]oct-6-ene. This reaction is commonly used to check for the presence of cyclopropene, following its synthesis.<sup id="cite_ref-Binger_9-1" class="reference"><a href="#cite_note-Binger-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:CyclopropeneDielsAlder.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/CyclopropeneDielsAlder.PNG/350px-CyclopropeneDielsAlder.PNG" decoding="async" width="350" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/CyclopropeneDielsAlder.PNG/525px-CyclopropeneDielsAlder.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/CyclopropeneDielsAlder.PNG/700px-CyclopropeneDielsAlder.PNG 2x" data-file-width="1660" data-file-height="421" /></a><figcaption></figcaption></figure></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Related_compounds">Related compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyclopropene&action=edit&section=7" title="Edit section: Related compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Malvalic_acid" title="Malvalic acid">Malvalic acid</a> is a toxic cyclopropene fatty acid that occurs in cottonseed oil.</li> <li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">1-Methylcyclopropene</a> (1-MCP) is used to slow the ripening in fruits.<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><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Borirene" class="mw-redirect" title="Borirene">Borirenes</a>, <a href="/wiki/Phosphirene" title="Phosphirene">phosphirenes</a>, and <a href="/w/index.php?title=Silirene&action=edit&redlink=1" class="new" title="Silirene (page does not exist)">silirenes</a> are boron-, phosphorus-, and silicon-substituted cyclopropenes, with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RBC<sub class="template-chem2-sub">2</sub>R'<sub class="template-chem2-sub">2</sub>, RPC<sub class="template-chem2-sub">2</sub>R'<sub class="template-chem2-sub">2</sub></span>, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>SiC<sub class="template-chem2-sub">2</sub>R'<sub class="template-chem2-sub">2</sub></span>.</li> <li><a href="/wiki/Cyclopropane_fatty_acid#Cyclopropene_fatty_acids" title="Cyclopropane fatty acid">Cyclopropene fatty acids</a> a class of naturally occurring cyclopropenes.</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=Cyclopropene&action=edit&section=8" 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-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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=123173&loc=ec_rcs">"cyclopropene - Compound Summary"</a>. <i>PubChem Compound</i>. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records<span class="reference-accessdate">. Retrieved <span class="nowrap">9 October</span> 2011</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem+Compound&rft.atitle=cyclopropene+-+Compound+Summary&rft.pages=Identification+and+Related+Records&rft.date=2005-03-27&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fsummary%2Fsummary.cgi%3Fcid%3D123173%26loc%3Dec_rcs&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFCarter,_F._L.Frampton,_V._L.1964" class="citation journal cs1">Carter, F. L.; Frampton, V. L. (1964). "Review of the Chemistry of Cyclopropene Compounds". <i>Chemical Reviews</i>. <b>64</b> (5): 497–525. <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%2Fcr60231a001">10.1021/cr60231a001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Review+of+the+Chemistry+of+Cyclopropene+Compounds&rft.volume=64&rft.issue=5&rft.pages=497-525&rft.date=1964&rft_id=info%3Adoi%2F10.1021%2Fcr60231a001&rft.au=Carter%2C+F.+L.&rft.au=Frampton%2C+V.+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFStaley,_S._W.Norden,_T._D.Su,_C.-F.Rall,_M.1987" class="citation journal cs1">Staley, S. W.; Norden, T. D.; Su, C.-F.; Rall, M.; Harmony, M. D. (1987). "Structure of 3-cyanocyclopropene by microwave spectroscopy and ab initio molecular orbital calculations. Evidence for substituent-ring double bond interactions". <i>J. Am. Chem. Soc</i>. <b>109</b> (10): 2880–2884. <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%2Fja00244a004">10.1021/ja00244a004</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Structure+of+3-cyanocyclopropene+by+microwave+spectroscopy+and+ab+initio+molecular+orbital+calculations.+Evidence+for+substituent-ring+double+bond+interactions&rft.volume=109&rft.issue=10&rft.pages=2880-2884&rft.date=1987&rft_id=info%3Adoi%2F10.1021%2Fja00244a004&rft.au=Staley%2C+S.+W.&rft.au=Norden%2C+T.+D.&rft.au=Su%2C+C.-F.&rft.au=Rall%2C+M.&rft.au=Harmony%2C+M.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllen,_F._H.1982" class="citation journal cs1">Allen, F. H. (1982). "The geometry of small rings: Molecular geometry of cyclopropene and its derivatives". <i>Tetrahedron</i>. <b>38</b> (5): 645–655. <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%2F0040-4020%2882%2980206-8">10.1016/0040-4020(82)80206-8</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=The+geometry+of+small+rings%3A+Molecular+geometry+of+cyclopropene+and+its+derivatives&rft.volume=38&rft.issue=5&rft.pages=645-655&rft.date=1982&rft_id=info%3Adoi%2F10.1016%2F0040-4020%2882%2980206-8&rft.au=Allen%2C+F.+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHartKarabatsos1966" class="citation book cs1">Hart, Harold; Karabatsos, G. J. (1966). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=qhwSBQAAQBAJ"><i>Advances in Alicyclic Chemistry</i></a>. Vol. 1. New York and London: Academic Press Inc. p. 55. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781483224206" title="Special:BookSources/9781483224206"><bdi>9781483224206</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advances+in+Alicyclic+Chemistry&rft.place=New+York+and+London&rft.pages=55&rft.pub=Academic+Press+Inc.&rft.date=1966&rft.isbn=9781483224206&rft.aulast=Hart&rft.aufirst=Harold&rft.au=Karabatsos%2C+G.+J.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DqhwSBQAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFSchlatter1941" class="citation journal cs1">Schlatter, Maurice J. (1941-06-01). <a rel="nofollow" class="external text" href="https://doi.org/10.1021/ja01851a068">"The Preparation of Cyclopropene"</a>. <i>Journal of the American Chemical Society</i>. <b>63</b> (6): 1733–1737. <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%2Fja01851a068">10.1021/ja01851a068</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</a>.</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=The+Preparation+of+Cyclopropene&rft.volume=63&rft.issue=6&rft.pages=1733-1737&rft.date=1941-06-01&rft_id=info%3Adoi%2F10.1021%2Fja01851a068&rft.issn=0002-7863&rft.aulast=Schlatter&rft.aufirst=Maurice+J.&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%2Fja01851a068&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFde_Meijere1997" class="citation book cs1 cs1-prop-long-vol">de Meijere, Armin, ed. (1997). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GVeGAwAAQBAJ&dq=alder+jacobs+cyclopropene+1528&pg=PA2713"><i>Houben-Weyl. Methods of Organic Chemistry – Cyclopropanes, Authors Index, Compound Index</i></a>. Vol. E 17d. Stuttgart, New York: George Thieme Verlag. pp. 2712–2713. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-13-101644-7" title="Special:BookSources/978-3-13-101644-7"><bdi>978-3-13-101644-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Houben-Weyl.+Methods+of+Organic+Chemistry+%E2%80%93+Cyclopropanes%2C+Authors+Index%2C+Compound+Index&rft.place=Stuttgart%2C+New+York&rft.pages=2712-2713&rft.pub=George+Thieme+Verlag&rft.date=1997&rft.isbn=978-3-13-101644-7&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGVeGAwAAQBAJ%26dq%3Dalder%2Bjacobs%2Bcyclopropene%2B1528%26pg%3DPA2713&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFCloss,_G.L.Krantz,_K.D.1966" class="citation journal cs1">Closs, G.L.; Krantz, K.D. (1966). "A Simple Synthesis of Cyclopropene". <i>Journal of Organic Chemistry</i>. <b>31</b> (2): 638. <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%2Fjo01340a534">10.1021/jo01340a534</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+Organic+Chemistry&rft.atitle=A+Simple+Synthesis+of+Cyclopropene&rft.volume=31&rft.issue=2&rft.pages=638&rft.date=1966&rft_id=info%3Adoi%2F10.1021%2Fjo01340a534&rft.au=Closs%2C+G.L.&rft.au=Krantz%2C+K.D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" class="Z3988"></span></span> </li> <li id="cite_note-Binger-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Binger_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Binger_9-1"><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="CITEREFBinger,_P.Wedermann,_P.Brinker,_U._H.2000" class="citation journal cs1">Binger, P.; Wedermann, P.; Brinker, U. H. (2000). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=v77p0254">"Cyclopropene: A New Simple Synthesis and Its Diels-Alder reaction with Cyclopentadiene"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>77</b>: 254</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Cyclopropene%3A+A+New+Simple+Synthesis+and+Its+Diels-Alder+reaction+with+Cyclopentadiene&rft.volume=77&rft.pages=254&rft.date=2000&rft.au=Binger%2C+P.&rft.au=Wedermann%2C+P.&rft.au=Brinker%2C+U.+H.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dv77p0254&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol. 10, p. 231</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=231&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFClarke,_T._C.Duncan,_C._D.Magid,_R._M.1971" class="citation journal cs1">Clarke, T. C.; Duncan, C. D.; Magid, R. M. (1971). "An Efficient and Convenient Synthesis of 1-Methylcyclopropene". <i>J. Org. Chem</i>. <b>36</b> (9): 1320–1321. <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%2Fjo00808a041">10.1021/jo00808a041</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=An+Efficient+and+Convenient+Synthesis+of+1-Methylcyclopropene&rft.volume=36&rft.issue=9&rft.pages=1320-1321&rft.date=1971&rft_id=info%3Adoi%2F10.1021%2Fjo00808a041&rft.au=Clarke%2C+T.+C.&rft.au=Duncan%2C+C.+D.&rft.au=Magid%2C+R.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFBeaudry,_R.Watkins,_C.2001" class="citation journal cs1">Beaudry, R.; Watkins, C. (2001). "Use of 1-MCP on Apples". <i>Perishable Handling Quarterly</i> (108). <a href="/wiki/University_of_California" title="University of California">University of California</a>: 12.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Perishable+Handling+Quarterly&rft.atitle=Use+of+1-MCP+on+Apples&rft.issue=108&rft.pages=12&rft.date=2001&rft.au=Beaudry%2C+R.&rft.au=Watkins%2C+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" 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="CITEREFTrinchero,_G._D.Sozzi,_G._O.Covatta,_F.Fraschina,_A._A.2004" class="citation journal cs1">Trinchero, G. D.; Sozzi, G. O.; Covatta, F.; Fraschina, A. A. (May 2004). "Inhibition of ethylene action by 1-methylcyclopropene extends postharvest life of "Bartlett" pears". <i>Postharvest Biology and Technology</i>. <b>32</b> (2): 193–204. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.postharvbio.2003.11.009">10.1016/j.postharvbio.2003.11.009</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Postharvest+Biology+and+Technology&rft.atitle=Inhibition+of+ethylene+action+by+1-methylcyclopropene+extends+postharvest+life+of+%22Bartlett%22+pears&rft.volume=32&rft.issue=2&rft.pages=193-204&rft.date=2004-05&rft_id=info%3Adoi%2F10.1016%2Fj.postharvbio.2003.11.009&rft.au=Trinchero%2C+G.+D.&rft.au=Sozzi%2C+G.+O.&rft.au=Covatta%2C+F.&rft.au=Fraschina%2C+A.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyclopropene" class="Z3988"></span></span> </li> </ol></div></div> <div 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.navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Cycloalkenes" 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" 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abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cycloalkenes" title="Template:Cycloalkenes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cycloalkenes" title="Template talk:Cycloalkenes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cycloalkenes" title="Special:EditPage/Template:Cycloalkenes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cycloalkenes" style="font-size:114%;margin:0 4em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkene" title="Alkene">Alkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclobutadiene" title="Cyclobutadiene">Cyclobutadiene</a></li> <li><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">Cyclopentadiene</a></li> <li>Cyclohexadiene <ul><li><a href="/wiki/1,3-Cyclohexadiene" class="mw-redirect" title="1,3-Cyclohexadiene">1,3-Cyclohexadiene</a></li> <li><a href="/wiki/1,4-Cyclohexadiene" class="mw-redirect" title="1,4-Cyclohexadiene">1,4-Cyclohexadiene</a></li></ul></li> <li>Cycloheptadiene <ul><li><a href="/wiki/1,3-Cycloheptadiene" title="1,3-Cycloheptadiene">1,3-Cycloheptadiene</a></li> <li><a href="/wiki/1,4-Cycloheptadiene" title="1,4-Cycloheptadiene">1,4-Cycloheptadiene</a></li></ul></li> <li><a href="/wiki/Cyclooctadiene" title="Cyclooctadiene">Cyclooctadiene</a> <ul><li><a href="/wiki/1,5-Cyclooctadiene" title="1,5-Cyclooctadiene">1,5-Cyclooctadiene</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triene" class="mw-redirect" title="Triene">Trienes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">Cycloheptatriene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetraenes</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclononatetraene" title="Cyclononatetraene">Cyclononatetraene</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"></div><div role="navigation" class="navbox" aria-labelledby="Annulenes" 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:Annulenes" title="Template:Annulenes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Annulenes" title="Template talk:Annulenes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Annulenes" title="Special:EditPage/Template:Annulenes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Annulenes" style="font-size:114%;margin:0 4em"><a href="/wiki/Annulene" title="Annulene">Annulenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Even–numbered</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclobutadiene" title="Cyclobutadiene">Cyclobutadiene</a></li> <li><i><a href="/wiki/Benzene" title="Benzene">Benzene</a></i></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclodecapentaene" title="Cyclodecapentaene">Cyclodecapentaene</a></li> <li><a href="/wiki/Cyclododecahexaene" title="Cyclododecahexaene">Cyclododecahexaene</a></li> <li><i><a href="/wiki/Cyclotetradecaheptaene" title="Cyclotetradecaheptaene">Cyclotetradecaheptaene</a></i></li> <li><a href="/wiki/Cyclohexadecaoctaene" class="mw-redirect" title="Cyclohexadecaoctaene">Cyclohexadecaoctaene</a></li> <li><i><a href="/wiki/Cyclooctadecanonaene" title="Cyclooctadecanonaene">Cyclooctadecanonaene</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Odd–numbered</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Cyclopropene</a></li> <li><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">Cyclopentadiene</a></li> <li><a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">Cycloheptatriene</a></li> <li><a href="/wiki/Cyclononatetraene" title="Cyclononatetraene">Cyclononatetraene</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>Compounds in <i>italics</i> are <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a></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" 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