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

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

1,* email, 1email, 1email, 1email, 1email, 1email and 2email
Received: 19 December 2013; in revised form: 10 January 2014 / Accepted: 15 January 2014 / Published: 27 January 2014
(This article belongs to the Special Issue Gas Phase Reactions)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
PDF Full-text Download PDF Full-Text [389 KB, uploaded 18 June 2014 20:25 CEST]

Export to BibTeX |
EndNote


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.

AMA Style

Leber PA, Nocket AJ, Hancock-Cerutti W, Bemis CY, Khine WK, Mohrbacher III JA, Baldwin JE. Gas Phase Thermal Reactions of exo-8-Cyclopropyl-bicyclo[4.2.0]oct-2-ene (1-exo). Molecules. 2014; 19(2):1527-1543.

Chicago/Turabian Style

Leber, Phyllis A.; Nocket, Anthony J.; Hancock-Cerutti, William; Bemis, Christopher Y.; Khine, Wint K.; Mohrbacher III, Joseph A.; Baldwin, John E. 2014. "Gas Phase Thermal Reactions of exo-8-Cyclopropyl-bicyclo[4.2.0]oct-2-ene (1-exo)." Molecules 19, no. 2: 1527-1543.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert