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Available in 30 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-30" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%B1%D9%83%D8%A8_%D8%A3%D9%84%D9%8A%D9%81%D8%A7%D8%AA%D9%8A_%D8%AD%D9%84%D9%82%D9%8A" title="مركب أليفاتي حلقي – Arabic" lang="ar" hreflang="ar" data-title="مركب أليفاتي حلقي" 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/Compost_alic%C3%ADclic" title="Compost alicíclic – Catalan" lang="ca" hreflang="ca" data-title="Compost alicíclic" 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/Alicyklick%C3%A9_slou%C4%8Deniny" title="Alicyklické sloučeniny – Czech" lang="cs" hreflang="cs" data-title="Alicyklické sloučeniny" 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/Alicyclische_Verbindungen" title="Alicyclische Verbindungen – German" lang="de" hreflang="de" data-title="Alicyclische Verbindungen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Alits%C3%BCklilised_%C3%BChendid" title="Alitsüklilised ühendid – Estonian" lang="et" hreflang="et" data-title="Alitsüklilised ühendid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%B5%CE%B9%CE%BA%CF%85%CE%BA%CE%BB%CE%B9%CE%BA%CE%AE_%CE%AD%CE%BD%CF%89%CF%83%CE%B7" title="Αλεικυκλική ένωση – Greek" lang="el" hreflang="el" data-title="Αλεικυκλική ένωση" 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/Compuesto_alic%C3%ADclico" title="Compuesto alicíclico – Spanish" lang="es" hreflang="es" data-title="Compuesto alicíclico" 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/Aliciklaj_kombina%C4%B5oj" title="Aliciklaj kombinaĵoj – Esperanto" lang="eo" hreflang="eo" data-title="Aliciklaj kombinaĵoj" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DA%A9%DB%8C%D8%A8%E2%80%8C%D9%87%D8%A7%DB%8C_%D8%A2%D9%84%DB%8C%D9%81%D8%A7%D8%AA%DB%8C%DA%A9_%D8%AD%D9%84%D9%82%D9%88%DB%8C" title="ترکیب‌های آلیفاتیک حلقوی – Persian" lang="fa" hreflang="fa" data-title="ترکیب‌های آلیفاتیک حلقوی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Compos%C3%A9_alicyclique" title="Composé alicyclique – French" lang="fr" hreflang="fr" data-title="Composé alicyclique" 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%A7%80%EB%B0%A9%EC%A1%B1_%EA%B3%A0%EB%A6%AC_%ED%99%94%ED%95%A9%EB%AC%BC" title="지방족 고리 화합물 – Korean" lang="ko" hreflang="ko" data-title="지방족 고리 화합물" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Senyawa_alisiklik" title="Senyawa alisiklik – Indonesian" lang="id" hreflang="id" data-title="Senyawa alisiklik" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Composti_aliciclici" title="Composti aliciclici – Italian" lang="it" hreflang="it" data-title="Composti aliciclici" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%AA%D7%A8%D7%9B%D7%95%D7%91%D7%AA_%D7%90%D7%9C%D7%99%D7%A6%D7%99%D7%A7%D7%9C%D7%99%D7%AA" title="תרכובת אליציקלית – Hebrew" lang="he" hreflang="he" data-title="תרכובת אליציקלית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%B2%E0%B2%BF%E0%B2%B8%E0%B3%88%E0%B2%95%E0%B3%8D%E0%B2%B2%E0%B2%BF%E0%B2%95%E0%B3%8D_%E0%B2%B8%E0%B2%82%E0%B2%AF%E0%B3%81%E0%B2%95%E0%B3%8D%E0%B2%A4" title="ಆಲಿಸೈಕ್ಲಿಕ್ ಸಂಯುಕ್ತ – Kannada" lang="kn" hreflang="kn" data-title="ಆಲಿಸೈಕ್ಲಿಕ್ ಸಂಯುಕ್ತ" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Aliciklusos_vegy%C3%BCletek" title="Aliciklusos vegyületek – Hungarian" lang="hu" hreflang="hu" data-title="Aliciklusos vegyületek" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%86%E0%B4%B2%E0%B4%BF%E0%B4%B8%E0%B5%88%E0%B4%95%E0%B5%8D%E0%B4%B2%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%B8%E0%B4%82%E0%B4%AF%E0%B5%81%E0%B4%95%E0%B5%8D%E0%B4%A4%E0%B4%99%E0%B5%8D%E0%B4%99%E0%B5%BE" title="ആലിസൈക്ലിക് സംയുക്തങ്ങൾ – Malayalam" lang="ml" hreflang="ml" data-title="ആലിസൈക്ലിക് സംയുക്തങ്ങൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alicyclische_verbinding" title="Alicyclische verbinding – Dutch" lang="nl" hreflang="nl" data-title="Alicyclische verbinding" 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/%E8%84%82%E7%92%B0%E5%BC%8F%E5%8C%96%E5%90%88%E7%89%A9" title="脂環式化合物 – Japanese" lang="ja" hreflang="ja" data-title="脂環式化合物" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Alitsiklik_birikmalar" title="Alitsiklik birikmalar – Uzbek" lang="uz" hreflang="uz" data-title="Alitsiklik birikmalar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Composto_alic%C3%ADclico" title="Composto alicíclico – Portuguese" lang="pt" hreflang="pt" data-title="Composto alicíclico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Compus_aliciclic" title="Compus aliciclic – Romanian" lang="ro" hreflang="ro" data-title="Compus aliciclic" 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%90%D0%BB%D0%B8%D1%86%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D1%81%D0%BE%D0%B5%D0%B4%D0%B8%D0%BD%D0%B5%D0%BD%D0%B8%D1%8F" title="Алициклические соединения – Russian" lang="ru" hreflang="ru" data-title="Алициклические соединения" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Alicyklick%C3%A1_zl%C3%BA%C4%8Denina" title="Alicyklická zlúčenina – Slovak" lang="sk" hreflang="sk" data-title="Alicyklická zlúčenina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Alicikli%C4%8Dna_spojina" title="Aliciklična spojina – Slovenian" lang="sl" hreflang="sl" data-title="Aliciklična spojina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Alicykliska_f%C3%B6reningar" title="Alicykliska föreningar – Swedish" lang="sv" hreflang="sv" data-title="Alicykliska föreningar" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Alisiklik_bile%C5%9Fik" title="Alisiklik bileşik – Turkish" lang="tr" hreflang="tr" data-title="Alisiklik bileşik" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BB%D1%96%D1%86%D0%B8%D0%BA%D0%BB%D1%96%D1%87%D0%BD%D1%96_%D1%81%D0%BF%D0%BE%D0%BB%D1%83%D0%BA%D0%B8" title="Аліциклічні сполуки – Ukrainian" lang="uk" hreflang="uk" data-title="Аліциклічні сполуки" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%DB%8C%D9%84%DB%8C_%D8%B3%D8%A7%D8%A6%DB%8C%DA%A9%D9%84%DA%A9_%D9%85%D8%B1%DA%A9%D8%A8%D8%A7%D8%AA" title="ایلی سائیکلک مرکبات – Urdu" lang="ur" hreflang="ur" data-title="ایلی سائیکلک مرکبات" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%84%82%E7%8E%AF%E6%97%8F%E5%8C%96%E5%90%88%E7%89%A9" title="脂环族化合物 – Chinese" lang="zh" hreflang="zh" data-title="脂环族化合物" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q155368#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul 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i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Carbon ring" redirects here. For aromatic carbon rings, see <a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a>.</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclopropane.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Cyclopropane.svg/150px-Cyclopropane.svg.png" decoding="async" width="150" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Cyclopropane.svg/225px-Cyclopropane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Cyclopropane.svg/300px-Cyclopropane.svg.png 2x" data-file-width="123" data-file-height="89" /></a><figcaption><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a> is the smallest alicyclic compound.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>alicyclic compound</b> contains one or more all-carbon <a href="/wiki/Cyclic_compound" title="Cyclic compound">rings</a> which may be either <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">saturated or unsaturated</a>, but do not have <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> character.<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> Alicyclic compounds may have one or more <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> <a href="/wiki/Side_chains" class="mw-redirect" title="Side chains">side chains</a> attached. </p><p>The simplest alicyclic compounds are the monocyclic <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>: <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a>, <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a>, <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a>, <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>, <a href="/wiki/Cycloheptane" title="Cycloheptane">cycloheptane</a>, <a href="/wiki/Cyclooctane" title="Cyclooctane">cyclooctane</a>, and so on. <a href="/wiki/Bicyclic_molecule" title="Bicyclic molecule">Bicyclic</a> alkanes include <a href="/wiki/Bicycloundecane" title="Bicycloundecane">bicycloundecane</a>, <a href="/wiki/Decalin" title="Decalin">decalin</a>, and <a href="/wiki/Housane" title="Housane">housane</a>. <a href="/wiki/Polycyclic_compound" title="Polycyclic compound">Polycyclic</a> alkanes include <a href="/wiki/Cubane" title="Cubane">cubane</a>, <a href="/wiki/Basketane" title="Basketane">basketane</a>, and <a href="/wiki/Tetrahedrane" title="Tetrahedrane">tetrahedrane</a>. </p><p><a href="/wiki/Spiro_compound" title="Spiro compound">Spiro compounds</a> have two or more rings that are connected through only one carbon atom. </p><p>The mode of ring-closing in the formation of many alicyclic compounds can be predicted by <a href="/wiki/Baldwin%27s_rules" title="Baldwin's rules">Baldwin's rules</a>. </p><p><a href="/wiki/Otto_Wallach" title="Otto Wallach">Otto Wallach</a>, a German chemist, received the 1910 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> for his work on alicyclic compounds.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Cycloalkenes">Cycloalkenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alicyclic_compound&action=edit&section=1" title="Edit section: Cycloalkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkene</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclohexene_structures.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Cyclohexene_structures.svg/220px-Cyclohexene_structures.svg.png" decoding="async" width="220" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Cyclohexene_structures.svg/330px-Cyclohexene_structures.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Cyclohexene_structures.svg/440px-Cyclohexene_structures.svg.png 2x" data-file-width="1131" data-file-height="326" /></a><figcaption><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a> is an alicyclic compound with a double bond.</figcaption></figure> <p>Monocyclic <a href="/wiki/Cycloalkene" title="Cycloalkene">cycloalkenes</a> are <a href="/wiki/Cyclopropene" title="Cyclopropene">cyclopropene</a>, <a href="/wiki/Cyclobutene" title="Cyclobutene">cyclobutene</a>, <a href="/wiki/Cyclopentene" title="Cyclopentene">cyclopentene</a>, <a href="/wiki/Cyclohexene" title="Cyclohexene">cyclohexene</a>, <a href="/wiki/Cycloheptene" title="Cycloheptene">cycloheptene</a>, <a href="/wiki/Cyclooctene" title="Cyclooctene">cyclooctene</a>, and so on. Bicyclic alkenes include <a href="/wiki/Norbornene" title="Norbornene">norbornene</a> and <a href="/wiki/Norbornadiene" title="Norbornadiene">norbornadiene</a>. </p><p>Two more examples are shown below, <a href="/wiki/Methylenecyclohexane" title="Methylenecyclohexane">methylenecyclohexane</a> on the left and <a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">1-methylcyclohexene</a> on the right: <span class="anchor" id="Exocyclic"></span> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Exocyclic.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Exocyclic.svg/200px-Exocyclic.svg.png" decoding="async" width="200" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Exocyclic.svg/300px-Exocyclic.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Exocyclic.svg/400px-Exocyclic.svg.png 2x" data-file-width="405" data-file-height="240" /></a><figcaption>Left: exocyclic double bond<br />Right: regular double bond</figcaption></figure> <p>An <b>exocyclic</b> group is always shown outside the ring structure, take for instance the exocyclic double bond of the former molecule. <a href="/wiki/Isotoluene" title="Isotoluene">Isotoluenes</a> are a prominent class of compounds with exocyclic double bonds. </p><p>The placement of double bonds in many alicyclic compounds can be predicted with <a href="/wiki/Bredt%27s_rule" title="Bredt's rule">Bredt's rule</a>. </p> <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=Alicyclic_compound&action=edit&section=2" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (1995) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00216.html">Alicyclic compounds</a>". <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><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00216">10.1351/goldbook.A00216</a></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="CITEREFLeopold_Ruzicka1932" class="citation journal cs1"><a href="/wiki/Leopold_Ruzicka" class="mw-redirect" title="Leopold Ruzicka">Leopold Ruzicka</a> (1932). "Third Pedler lecture. The life and work of Otto Wallach". <i><a href="/wiki/J._Chem._Soc." class="mw-redirect" title="J. Chem. Soc.">J. Chem. Soc.</a></i>: 1582. <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%2FJR9320001582">10.1039/JR9320001582</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.&rft.atitle=Third+Pedler+lecture.+The+life+and+work+of+Otto+Wallach&rft.pages=1582&rft.date=1932&rft_id=info%3Adoi%2F10.1039%2FJR9320001582&rft.au=Leopold+Ruzicka&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlicyclic+compound" 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="CITEREFChristmann2010" class="citation journal cs1">Christmann, M (2010). "Otto Wallach: Founder of Terpene Chemistry and Nobel Laureate 1910". <i>Angewandte Chemie International Edition</i>. <b>49</b> (50): 9580–9586. <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%2Fanie.201003155">10.1002/anie.201003155</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/21110354">21110354</a>.</cite><span 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