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Synthesis

It can be prepared by base-catalyzed isomerization of 2,3-dimethyl-1-butene.¹ Another route involves direct dimerization of propylene.² It can also be produced by photolysis of tetramethylcyclobutane-1,3-dione.³

Reactions

Tetramethylethylene forms metal-alkene complexes with low-valent metals and reacts with diborane to give the monoalkyborane known as thexylborane.⁴⁵

Oxidation gives pinacol.

It is a precursor to the herbicide fenpropathrin.⁶

References

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. /wiki/Doi_(identifier) ↩

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. https://hal-ifp.archives-ouvertes.fr/hal-02954532/file/Nickel%20Catalyzed%20Olefin.pdf ↩

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) /wiki/Doi_(identifier) ↩

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. /wiki/Doi_(identifier) ↩

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. 9780471526193 ↩

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. https://hal-ifp.archives-ouvertes.fr/hal-02954532/file/Nickel%20Catalyzed%20Olefin.pdf ↩