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Molecules 2014, 19(2), 1527-1543; doi:10.3390/molecules19021527

Gas Phase Thermal Reactions of exo-8-Cyclopropyl-bicyclo[4.2.0]oct-2-ene (1-exo)

1
Department of Chemistry, Franklin & Marshall College, Lancaster, PA 17604-3003, USA
2
Department of Chemistry, Syracuse University, Syracuse, NY 13244-4100, USA
*
Author to whom correspondence should be addressed.
Received: 19 December 2013 / Revised: 10 January 2014 / Accepted: 15 January 2014 / Published: 27 January 2014
(This article belongs to the Special Issue Gas Phase Reactions)
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Abstract

The title compound 1-exo (with minor amounts of its C8 epimer 1-endo) was prepared by Wolff-Kishner reduction of the cycloadduct of 1,3-cyclohexadiene and cyclopropylketene. The [1,3]-migration product 2-endo was synthesized by efficient selective cyclopropanation of endo-5-vinylbicyclo[2.2.2]oct-2-ene at the exocyclic π-bond. Gas phase thermal reactions of 1-exo afforded C8 epimerization to 1-endo, [1,3]- migrations to 2-exo and 2-endo, direct fragmentation to cyclohexadiene and vinylcyclopropane, and CPC rearrangement in the following relative kinetic order: kep > k13 > kf > kCPC.
Keywords: gas phase reaction; thermal chemistry; [1,3]-sigmatropic rearrangement; [1,3]-carbon migration; CPC rearrangement gas phase reaction; thermal chemistry; [1,3]-sigmatropic rearrangement; [1,3]-carbon migration; CPC rearrangement
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Leber, P.A.; Nocket, A.J.; Hancock-Cerutti, W.; Bemis, C.Y.; Khine, W.K.; Mohrbacher III, J.A.; Baldwin, J.E. Gas Phase Thermal Reactions of exo-8-Cyclopropyl-bicyclo[4.2.0]oct-2-ene (1-exo). Molecules 2014, 19, 1527-1543.

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