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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Intramolecular reaction</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Reacci%C3%B3_intramolecular" title="Reacció intramolecular – Catalan" lang="ca" hreflang="ca" data-title="Reacció intramolecular" 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/Vnitromolekul%C3%A1rn%C3%AD_reakce" title="Vnitromolekulární reakce – Czech" lang="cs" hreflang="cs" data-title="Vnitromolekulární reakce" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Intramolekyl%C3%A6r" title="Intramolekylær – Danish" lang="da" hreflang="da" data-title="Intramolekylær" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Intramolekulaarne_reaktsioon" title="Intramolekulaarne reaktsioon – Estonian" lang="et" hreflang="et" data-title="Intramolekulaarne reaktsioon" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Intramolecular" title="Intramolecular – Spanish" lang="es" hreflang="es" data-title="Intramolecular" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%D8%A7%DA%A9%D9%86%D8%B4_%D8%AF%D8%B1%D9%88%D9%86_%D9%85%D9%88%D9%84%DA%A9%D9%88%D9%84%DB%8C" title="واکنش درون مولکولی – Persian" lang="fa" hreflang="fa" data-title="واکنش درون مولکولی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/R%C3%A9action_intramol%C3%A9culaire" title="Réaction intramoléculaire – French" lang="fr" hreflang="fr" data-title="Réaction intramoléculaire" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Intramoleculaire_reactie" title="Intramoleculaire reactie – Dutch" lang="nl" hreflang="nl" data-title="Intramoleculaire reactie" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E5%88%86%E5%AD%90%E5%86%85%E5%8F%8D%E5%BF%9C" title="分子内反応 – Japanese" lang="ja" hreflang="ja" data-title="分子内反応" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Intramolecular" title="Intramolecular – Portuguese" lang="pt" hreflang="pt" data-title="Intramolecular" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Reac%C8%9Bie_intramolecular%C4%83" title="Reacție intramoleculară – Romanian" lang="ro" hreflang="ro" data-title="Reacție intramoleculară" 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%92%D0%BD%D1%83%D1%82%D1%80%D0%B8%D0%BC%D0%BE%D0%BB%D0%B5%D0%BA%D1%83%D0%BB%D1%8F%D1%80%D0%BD%D0%B0%D1%8F_%D1%80%D0%B5%D0%B0%D0%BA%D1%86%D0%B8%D1%8F" title="Внутримолекулярная реакция – Russian" lang="ru" hreflang="ru" data-title="Внутримолекулярная реакция" 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/Intramolekulska_reakcija" title="Intramolekulska reakcija – Serbian" lang="sr" hreflang="sr" data-title="Intramolekulska reakcija" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Intramolekyl%C3%A4r_reaktion" 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searchaux" style="display:none">Process or characteristic limited to the structure of a single molecule</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>intramolecular</b> describes a <a href="/wiki/Chemical_process" title="Chemical process">process</a> or characteristic limited within the <a href="/wiki/Chemical_structure" title="Chemical structure">structure</a> of a single <a href="/wiki/Molecule" title="Molecule">molecule</a>, a property or phenomenon limited to the extent of a single molecule. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Relative_rates">Relative rates</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Intramolecular_reaction&action=edit&section=1" title="Edit section: Relative rates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In intramolecular <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a>, two reaction sites are contained within a single molecule. This configuration elevates the effective <a href="/wiki/Concentration" title="Concentration">concentration</a> of the reacting partners resulting in high <a href="/wiki/Reaction_rate" title="Reaction rate">reaction rates</a>. Many intramolecular reactions are observed where the <a href="/wiki/Intermolecular" class="mw-redirect" title="Intermolecular">intermolecular</a> version does not take place. </p><p>Intramolecular reactions, especially ones leading to the formation of 5- and 6-membered rings, are rapid compared to an analogous intermolecular process. This is largely a consequence of the reduced entropic cost for reaching the transition state of ring formation and the absence of significant strain associated with formation of rings of these sizes. For the formation of different ring sizes via cyclization of substrates of varying tether length, the order of reaction rates (rate constants <i>k<sub>n</sub></i> for the formation of an <i>n</i>-membered ring) is usually <i>k</i><sub>5</sub> > <i>k</i><sub>6</sub> > <i>k</i><sub>3</sub> > <i>k</i><sub>7</sub> > <i>k</i><sub>4</sub> as shown below for a series of ω-bromoalkylamines. This somewhat complicated rate trend reflects the interplay of these entropic and strain factors: </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:SN2intramolecular.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/SN2intramolecular.png/320px-SN2intramolecular.png" decoding="async" width="320" height="47" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/SN2intramolecular.png/480px-SN2intramolecular.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/SN2intramolecular.png/640px-SN2intramolecular.png 2x" data-file-width="1394" data-file-height="204" /></a><figcaption></figcaption></figure> <table class="wikitable" style="margin-left: auto; margin-right: auto; border: none;"> <caption>Relative rate constants for cyclization (<i>n</i> = 5 set to <i>k</i><sub>rel</sub> = 100) </caption> <caption> </caption> <tbody><tr> <th><i>n</i> </th> <th><i>k</i><sub>rel</sub> </th> <th><i>n</i> </th> <th><i>k</i><sub>rel</sub> </th> <th><i>n</i> </th> <th><i>k</i><sub>rel</sub> </th></tr> <tr> <td>3 </td> <td>0.1 </td> <td>6 </td> <td>1.7 </td> <td>12 </td> <td>0.00001 </td></tr> <tr> <td>4 </td> <td>0.002 </td> <td>7 </td> <td>0.03 </td> <td>14 </td> <td>0.0003 </td></tr> <tr> <td>5 </td> <td>100 </td> <td>10 </td> <td>0.00000001 </td> <td>15 </td> <td>0.0003 </td></tr></tbody></table> <p>For the <b>'small rings'</b> (<i>3- and 4- membered</i>), the slow rates is a consequence of <a href="/wiki/Ring_strain" title="Ring strain">angle strain</a> experienced at the transition state. Although three-membered rings are more strained, formation of aziridine is faster than formation of azetidine due to the proximity of the leaving group and nucleophile in the former, which increases the probability that they would meet in a reactive conformation. The same reasoning holds for the <b>'unstrained rings'</b> (<i>5-, 6-, and 7-membered</i>). The formation of <b>'medium-sized rings'</b> (<i>8- to 13-membered</i>) is particularly disfavorable due to a combination of an increasingly unfavorable entropic cost and the additional presence of <a href="/wiki/Transannular_strain" class="mw-redirect" title="Transannular strain">transannular strain</a> arising from steric interactions across the ring. Finally, for <b>'large rings'</b> (<i>14-membered or higher</i>), the rate constants level off, as the distance between the leaving group and nucleophile is now so large the reaction is now effectively intermolecular.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Although the details may change somewhat, the general trends hold for a variety of intramolecular reactions, including radical-mediated and (in some cases) transition metal-catalyzed processes. </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Intramolecular_reaction&action=edit&section=2" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many reactions in organic chemistry can occur in either an intramolecular or intermolecular senses. Some reactions are by definition intramolecular or are only practiced intramolecularly, e.g., </p> <ul><li><a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a> of diesters is the intramolecular version of <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a>.</li> <li><a href="/wiki/Madelung_synthesis" title="Madelung synthesis">Madelung synthesis</a> of <a href="/wiki/Indole" title="Indole">indoles</a></li> <li><a href="/wiki/Smiles_rearrangement" title="Smiles rearrangement">Smiles rearrangement</a></li> <li><a href="/wiki/Hydroacylation" title="Hydroacylation">Hydroacylation</a> is almost invariably practiced intramolecularly to produce ketones.<sup id="cite_ref-Willis_3-0" class="reference"><a href="#cite_note-Willis-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul> <dl><dd>RCHO + CH<sub>2</sub>=CHR' → RC(O)CH<sub>2</sub>CH<sub>2</sub>R'</dd></dl> <ul><li><a href="/wiki/Nazarov_cyclization_reaction" title="Nazarov cyclization reaction">Nazarov cyclization reaction</a> for the synthesis of <a href="/wiki/Cyclopentenone" title="Cyclopentenone">cyclopentenones</a></li></ul> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Nazarov_cyclization.png" class="mw-file-description" title="The Nazarov cyclization reaction"><img alt="The Nazarov cyclization reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Nazarov_cyclization.png/320px-Nazarov_cyclization.png" decoding="async" width="320" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Nazarov_cyclization.png/480px-Nazarov_cyclization.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Nazarov_cyclization.png/640px-Nazarov_cyclization.png 2x" data-file-width="840" data-file-height="262" /></a><figcaption>The Nazarov cyclization reaction</figcaption></figure></dd></dl> <ul><li>The <a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a>, involving reductive coupling of alkyl halides, essentially is only useful when conducted intramolecularly. Its utility is illustrated with the synthesis of strained rings:<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></li></ul> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Wurtz-reaction_Bicyclobutane_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Wurtz-reaction_Bicyclobutane_synthesis.svg/300px-Wurtz-reaction_Bicyclobutane_synthesis.svg.png" decoding="async" width="300" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Wurtz-reaction_Bicyclobutane_synthesis.svg/450px-Wurtz-reaction_Bicyclobutane_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Wurtz-reaction_Bicyclobutane_synthesis.svg/600px-Wurtz-reaction_Bicyclobutane_synthesis.svg.png 2x" data-file-width="501" data-file-height="104" /></a><figcaption></figcaption></figure></dd></dl> <p>Some transformations that are enabled or enhanced intramolecularly. For example, the <a href="/wiki/Acyloin_condensation" title="Acyloin condensation">acyloin condensation</a> of diesters almost uniquely produces 10-membered carbocycles, which are difficult to construct otherwise.<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> Another example is the 2+2 cycloaddition of <a href="/wiki/Norbornadiene" title="Norbornadiene">norbornadiene</a> to give <a href="/wiki/Quadricyclane" title="Quadricyclane">quadricyclane</a>. </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Synthesis_of_quadricyclane_from_norbornadiene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Synthesis_of_quadricyclane_from_norbornadiene.png/350px-Synthesis_of_quadricyclane_from_norbornadiene.png" decoding="async" width="350" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Synthesis_of_quadricyclane_from_norbornadiene.png/525px-Synthesis_of_quadricyclane_from_norbornadiene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Synthesis_of_quadricyclane_from_norbornadiene.png/700px-Synthesis_of_quadricyclane_from_norbornadiene.png 2x" data-file-width="1586" data-file-height="406" /></a><figcaption></figcaption></figure></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Tools_and_concepts">Tools and concepts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Intramolecular_reaction&action=edit&section=3" title="Edit section: Tools and concepts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many tools and concepts have been developed to exploit the advantages of intramolecular cyclizations. For example, installing large substituents exploits the <a href="/wiki/Thorpe-Ingold_effect" class="mw-redirect" title="Thorpe-Ingold effect">Thorpe-Ingold effect</a>. <a href="/wiki/High_dilution_reaction" class="mw-redirect" title="High dilution reaction">High dilution reactions</a> suppress intermolecular processes. One set of tools involves tethering as discussed below. </p> <div class="mw-heading mw-heading3"><h3 id="Tethered_intramolecular_[2+2]_reactions"><span id="Tethered_intramolecular_.5B2.2B2.5D_reactions"></span><span id="Tethered_intramolecular_2+2_reactions">Tethered intramolecular [2+2] reactions</span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Intramolecular_reaction&action=edit&section=4" title="Edit section: Tethered intramolecular [2+2] reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tethered intramolecular [2+2] reactions entail the formation of <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a> and <a href="/wiki/Cyclobutanone" title="Cyclobutanone">cyclobutanone</a> via intramolecular <a href="/wiki/2%2B2_photocycloaddition" class="mw-redirect" title="2+2 photocycloaddition">2+2 photocycloadditions</a>. Tethering ensures formation of a multi-cyclic system. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:23_fig._1.png" class="mw-file-description" title="Tethered intramolecular [2+2] reactions"><img alt="Tethered intramolecular [2+2] reactions" src="//upload.wikimedia.org/wikipedia/commons/8/88/23_fig._1.png" decoding="async" width="407" height="244" class="mw-file-element" data-file-width="257" data-file-height="154" /></a><figcaption>Tethered intramolecular [2+2] reactions</figcaption></figure> <p>The length of the tether affects the <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemical outcome</a> of the [2+2] reaction. Longer tethers tend to generate the "straight" product where the terminal carbon of the alkene is linked to the <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 \alpha }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>α</mi> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \alpha }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/b79333175c8b3f0840bfb4ec41b8072c83ea88d3" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:1.488ex; height:1.676ex;" alt="{\displaystyle \alpha }"></span>-carbon of the <a href="/wiki/Alpha-beta_Unsaturated_carbonyl_compounds" class="mw-redirect" title="Alpha-beta Unsaturated carbonyl compounds">enone</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> When the tether consists only two carbons, the “bent” product is generated where the <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 \beta }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>β</mi> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \beta }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7ed48a5e36207156fb792fa79d29925d2f7901e8" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.671ex; width:1.332ex; height:2.509ex;" alt="{\displaystyle \beta }"></span>-carbon of the enone is connected to the terminal carbon of the alkene.<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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:23_fig._2.png" class="mw-file-description" title="Effects of the length of tether on [2+2] photocyclization reaction"><img alt="Effects of the length of tether on [2+2] photocyclization reaction" src="//upload.wikimedia.org/wikipedia/commons/8/82/23_fig._2.png" decoding="async" width="407" height="219" class="mw-file-element" data-file-width="255" data-file-height="137" /></a><figcaption>Effects of the length of tether on [2+2] photocyclization reaction</figcaption></figure> <p>Tethered [2+2] reactions have been used to synthesize organic compounds with interesting ring systems and <a href="/wiki/Topologies" class="mw-redirect" title="Topologies">topologies</a>. For example, [2+2] photocyclization was used to construct the tricyclic core structure in <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolide</a> B.<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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:23_fig._3.png" class="mw-file-description" title="Tethered [2+2] reaction in the total synthesis of (+) - Ginkgolide B"><img alt="Tethered [2+2] reaction in the total synthesis of (+) - Ginkgolide B" src="//upload.wikimedia.org/wikipedia/commons/1/14/23_fig._3.png" decoding="async" width="407" height="109" class="mw-file-element" data-file-width="316" data-file-height="85" /></a><figcaption>Tethered [2+2] reaction in the total synthesis of (<u>+)</u> - Ginkgolide B</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Molecular_tethers">Molecular tethers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Intramolecular_reaction&action=edit&section=5" title="Edit section: Molecular tethers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Otherwise-intermolecular reactions can be made temporarily intramolecular by linking both reactants by a <a href="/wiki/Tether" title="Tether">tether</a> with all the advantages associated to it. Popular choices of tether contain a <a href="/wiki/Carbonate_ester" title="Carbonate ester">carbonate ester</a>, <a href="/wiki/Boronic_ester" class="mw-redirect" title="Boronic ester">boronic ester</a>, <a href="/wiki/Silyl_ether" title="Silyl ether">silyl ether</a>, or a <a href="/wiki/Silyl_acetal" class="mw-redirect" title="Silyl acetal">silyl acetal</a> link (<b>silicon tethers</b>)<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><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> which are fairly inert in many organic reactions yet can be cleaved by specific reagents. The main hurdle for this strategy to work is selecting the proper length for the tether and making sure reactive groups have an optimal orientation with respect to each other. An examples is a <a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a> of an alkene and an alkyne tethered together via a silyl ether.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Pauson-Khand_Silicon_Tether.png" class="mw-file-description" title="Pauson-Khand silicon tether"><img alt="Pauson-Khand silicon tether" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Pauson-Khand_Silicon_Tether.png/300px-Pauson-Khand_Silicon_Tether.png" decoding="async" width="300" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Pauson-Khand_Silicon_Tether.png/450px-Pauson-Khand_Silicon_Tether.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Pauson-Khand_Silicon_Tether.png/600px-Pauson-Khand_Silicon_Tether.png 2x" data-file-width="706" data-file-height="412" /></a></span> </p><p>In this particular reaction, the tether angle bringing the reactive groups together is effectively reduced by placing <a href="/wiki/Isopropyl" class="mw-redirect" title="Isopropyl">isopropyl</a> groups on the silicon atom via the <a href="/wiki/Thorpe%E2%80%93Ingold_effect" title="Thorpe–Ingold effect">Thorpe–Ingold effect</a>. No reaction takes place when these bulky groups are replaced by smaller methyl groups. Another example is a <a href="/wiki/Photochemical" class="mw-redirect" title="Photochemical">photochemical</a> [2+2]<a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> with two alkene groups tethered through a silicon acetal group (racemic, the other <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> not depicted), which is subsequently cleaved by <a href="/wiki/TBAF" class="mw-redirect" title="TBAF">TBAF</a> yielding the endo-diol. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:CycloadditionSiliconTether.png" class="mw-file-description" title="Cycloaddition silicon tether"><img alt="Cycloaddition silicon tether" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/CycloadditionSiliconTether.png/400px-CycloadditionSiliconTether.png" decoding="async" width="400" height="296" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/CycloadditionSiliconTether.png/600px-CycloadditionSiliconTether.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/CycloadditionSiliconTether.png/800px-CycloadditionSiliconTether.png 2x" data-file-width="1013" data-file-height="749" /></a></span></dd></dl> <p>Without the tether, the <a href="/wiki/Exo_isomer" class="mw-redirect" title="Exo isomer">exo isomer</a> forms.<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> </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=Intramolecular_reaction&action=edit&section=6" 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 id="CITEREFStreitwieserHeathcockKosower2017" class="citation book cs1">Streitwieser, Andrew; Heathcock, Clayton H.; Kosower, Edward M. 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New Delhi: Medtech (Scientific International, reprint of 1998 revised 4th edition, Macmillan). p. 198. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9789385998898" title="Special:BookSources/9789385998898"><bdi>9789385998898</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Introduction+to+Organic+Chemistry&rft.place=New+Delhi&rft.pages=198&rft.pub=Medtech+%28Scientific+International%2C+reprint+of+1998+revised+4th+edition%2C+Macmillan%29&rft.date=2017&rft.isbn=9789385998898&rft.aulast=Streitwieser&rft.aufirst=Andrew&rft.au=Heathcock%2C+Clayton+H.&rft.au=Kosower%2C+Edward+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIntramolecular+reaction" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJonathan_Clayden2001" class="citation book cs1">Jonathan Clayden (2001). <a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00clay_0/page/454"><i>Organic chemistry</i></a>. 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Reaction_mechanisms" title="Template:Reaction mechanisms"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Reaction_mechanisms" title="Template talk:Reaction mechanisms"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Reaction_mechanisms" title="Special:EditPage/Template:Reaction mechanisms"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Basic_reaction_mechanisms" style="font-size:114%;margin:0 4em">Basic <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">reaction mechanisms</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">Nucleophilic substitutions</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/SN1_reaction" title="SN1 reaction">Unimolecular nucleophilic substitution</a> (S<sub>N</sub>1)</li> <li><a href="/wiki/SN2_reaction" title="SN2 reaction">Bimolecular nucleophilic substitution</a> (S<sub>N</sub>2)</li> <li><a href="/wiki/Nucleophilic_aromatic_substitution" title="Nucleophilic aromatic substitution">Nucleophilic aromatic substitution</a> (S<sub>N</sub>Ar)</li> <li><a href="/wiki/SNi" title="SNi">Nucleophilic internal substitution</a> (S<sub>N</sub>i)</li> <li><a href="/wiki/Nucleophilic_acyl_substitution" class="mw-redirect" title="Nucleophilic acyl substitution">Nucleophilic acyl substitution</a> (S<sub>N</sub>Acyl)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electrophilic_substitution" title="Electrophilic substitution">Electrophilic substitutions</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/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">Electrophilic aromatic substitution</a> (S<sub>E</sub>Ar)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reactions</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/E1_elimination" class="mw-redirect" title="E1 elimination">Unimolecular elimination</a> (E1)</li> <li><a href="/wiki/E1cB-elimination_reaction" title="E1cB-elimination reaction">E1cB-elimination</a></li> <li><a href="/wiki/E2_elimination" class="mw-redirect" title="E2 elimination">Bimolecular elimination</a> (E2)</li> <li><a href="/wiki/Ei_mechanism" title="Ei mechanism">E<sub>i</sub> elimination</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addition_reaction" title="Addition reaction">Addition reactions</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/Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a> (A<sub>E</sub>)</li> <li><a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">Nucleophilic addition</a> (A<sub>N</sub>)</li> <li><a href="/wiki/Free-radical_addition" title="Free-radical addition">Free-radical addition</a></li> <li><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></li> <li><a href="/wiki/Oxidative_addition" title="Oxidative addition">Oxidative addition</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unimolecular reactions</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">Intramolecular reaction</a></li> <li><a href="/wiki/Isomerization" title="Isomerization">Isomerization</a></li> <li><a href="/wiki/Photodissociation" title="Photodissociation">Photodissociation</a></li> <li><a href="/wiki/Lindemann%E2%80%93Hinshelwood_mechanism" class="mw-redirect" title="Lindemann–Hinshelwood mechanism">Lindemann–Hinshelwood mechanism</a></li> <li><a href="/wiki/RRKM_theory" title="RRKM theory">RRKM theory</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_transfer" title="Electron transfer">Electron/Proton transfer</a> reactions</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/Redox" title="Redox">Redox</a></li> <li><a href="/wiki/Harpoon_reaction" title="Harpoon reaction">Harpoon reaction</a></li> <li><a href="/wiki/Grotthuss_mechanism" title="Grotthuss mechanism">Grotthuss mechanism</a></li> <li><a href="/wiki/Marcus_theory" title="Marcus theory">Marcus theory</a></li> <li><a href="/wiki/Inner_sphere_electron_transfer" title="Inner sphere electron transfer">Inner sphere electron transfer</a></li> <li><a href="/wiki/Outer_sphere_electron_transfer" title="Outer sphere electron transfer">Outer sphere electron transfer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Medium effects</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/Solvent_effects" title="Solvent effects">Solvent effects</a></li> <li><a href="/wiki/Cage_effect" title="Cage effect">Cage effect</a></li> <li><a href="/wiki/Matrix_isolation" title="Matrix isolation">Matrix isolation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</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/Elementary_reaction" title="Elementary reaction">Elementary reaction</a></li> <li><a href="/wiki/Reaction_dynamics" title="Reaction dynamics">Reaction dynamics</a></li> <li><a href="/wiki/Reactive_intermediate" title="Reactive intermediate">Reactive intermediate</a></li> <li><a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">Radical (chemistry)</a></li> <li><a href="/wiki/Molecularity" title="Molecularity">Molecularity</a></li> <li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a></li> <li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li> <li><a href="/wiki/Collision_theory" title="Collision theory">Collision theory</a></li> <li><a href="/wiki/Arrow_pushing" title="Arrow pushing">Arrow pushing</a></li> <li><a href="/wiki/Potential_energy_surface" title="Potential energy surface">Potential energy surface</a></li> <li><a href="/wiki/More_O%27Ferrall%E2%80%93Jencks_plot" title="More O'Ferrall–Jencks plot">More O'Ferrall–Jencks plot</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</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/Rate_equation" title="Rate equation">Rate equation</a></li> <li><a href="/wiki/Equilibrium_constant" title="Equilibrium constant">Equilibrium constant</a></li> <li><a href="/wiki/Rate-determining_step" title="Rate-determining step">Rate-determining step</a></li> <li><a href="/wiki/Reaction_coordinate" title="Reaction coordinate">Reaction coordinate</a></li> <li><a href="/wiki/Energy_profile_(chemistry)" title="Energy profile (chemistry)">Energy profile (chemistry)</a></li> <li><a href="/wiki/Transition_state_theory" title="Transition state theory">Transition state theory</a></li> <li><a href="/wiki/Activation_energy" title="Activation energy">Activation energy</a></li> <li><a href="/wiki/Activated_complex" title="Activated complex">Activated complex</a></li> <li><a href="/wiki/Arrhenius_equation" title="Arrhenius equation">Arrhenius equation</a></li> <li><a href="/wiki/Eyring_equation" title="Eyring equation">Eyring equation</a></li> <li><a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">Michaelis–Menten kinetics</a></li> <li><a href="/wiki/Diffusion-controlled_reaction" title="Diffusion-controlled reaction">Diffusion-controlled reaction</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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