Tetramethylethylene

<h2 id="synthesis">Synthesis</h2>
It can be prepared by base-catalyzed isomerization of <a href="/facts/2%2c3-Dimethyl-1-butene/anVwSK7A">2,3-dimethyl-1-butene</a>.<a class="footnote-ref" id="fnref:1" href="#fn:1">1</a> Another route involves direct <a href="/facts/Dimer_(chemistry)/mU64PnEq">dimerization</a> of <a href="/facts/Propylene/5eLDmPvm">propylene</a>.<a class="footnote-ref" id="fnref:2" href="#fn:2">2</a> It can also be produced by photolysis of <a href="/facts/Tetramethylcyclobutane-1%2c3-dione/Djw8J7vk">tetramethylcyclobutane-1,3-dione</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3">3</a>

<h2 id="reactions">Reactions</h2>
Tetramethylethylene forms <a href="/facts/Metal-alkene_complex/QMNU6cno">metal-alkene complexes</a> with low-valent metals and reacts with <a href="/facts/Diborane/k7egwbPf">diborane</a> to give the monoalkyborane known as <a href="/facts/Thexylborane/lq6pISgn">thexylborane</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4">4</a><a class="footnote-ref" id="fnref:5" href="#fn:5">5</a>
Oxidation gives <a href="/facts/Pinacol/PfUrsYP1">pinacol</a>.
It is a precursor to the herbicide <a href="/facts/Fenpropathrin/0sEGLUPJ">fenpropathrin</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6">6</a>

<h2 id="references">References</h2>

<ol>
<li id="fn:1">Hattori, Hideshi (2001). "Solid base catalysts: Generation of basic sites and application to organic synthesis". Applied Catalysis A: General. 222 (1–2): 247–259. doi:10.1016/S0926-860X(01)00839-0. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></li>
<li id="fn:2">Olivier-Bourbigou, H.; Breuil, P. A. R.; Magna, L.; Michel, T.; Espada Pastor, M. Fernandez; Delcroix, D. (2020). "Nickel Catalyzed Olefin Oligomerization and Dimerization" (PDF). Chemical Reviews. 120 (15): 7919–7983. doi:10.1021/acs.chemrev.0c00076. PMID 32786672. S2CID 221124789. <a href="https://hal-ifp.archives-ouvertes.fr/hal-02954532/file/Nickel%20Catalyzed%20Olefin.pdf" target="_blank">https://hal-ifp.archives-ouvertes.fr/hal-02954532/file/Nickel%20Catalyzed%20Olefin.pdf</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></li>
<li id="fn:3">Nicholas J. Turro, Peter A. Leermakers, George F. Vesley (1967). "Cyclohexylidenecyclohexane". Organic Syntheses. 47: 34. doi:10.15227/orgsyn.047.0034.{{cite journal}}: CS1 maint: multiple names: authors list (link) <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></li>
<li id="fn:4">Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly Versatile Reagent for Organic Synthesis via Hydroboration". Synthesis. 1974 (2): 77–89. doi:10.1055/s-1974-23248. S2CID 96012955. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></li>
<li id="fn:5">Giordano, G.; Crabtree, R. H. (1990). "Di-μ-Chloro-Bis(η 4 -1,5-Cyclooctadiene)-Dirhodium(I)". Di-μ-Chloro-Bis(η4-1,5-Cyclooctadiene)-Dirhodium(I). Inorganic Syntheses. Vol. 28. pp. 88–90. doi:10.1002/9780470132593.ch22. ISBN 9780471526193. <a href="9780471526193" target="_blank">9780471526193</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></li>
<li id="fn:6">Olivier-Bourbigou, H.; Breuil, P. A. R.; Magna, L.; Michel, T.; Espada Pastor, M. Fernandez; Delcroix, D. (2020). "Nickel Catalyzed Olefin Oligomerization and Dimerization" (PDF). Chemical Reviews. 120 (15): 7919–7983. doi:10.1021/acs.chemrev.0c00076. PMID 32786672. S2CID 221124789. <a href="https://hal-ifp.archives-ouvertes.fr/hal-02954532/file/Nickel%20Catalyzed%20Olefin.pdf" target="_blank">https://hal-ifp.archives-ouvertes.fr/hal-02954532/file/Nickel%20Catalyzed%20Olefin.pdf</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></li>
</ol>

Tetramethylethylene open-in-new

Tetramethylethylene