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- Title
Gas Phase Thermal Reactions of exo-8-Cyclopropylbicyclo[ 4.2.0]oct-2-ene (1-exo).
- Authors
Leber, Phyllis A.; Nocket, Anthony J.; Hancock-Cerutti, William; Bemis, Christopher Y.; Khine, Wint Khant; Mohrbacher III, Joseph A.; Baldwin, John E.
- 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.
- Subjects
WOLFF-Kishner reduction; DEOXYGENATION; CHEMICAL reduction; EPIMERIZATION; CHEMICAL processes
- Publication
Molecules, 2014, Vol 19, Issue 2, p1527
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules19021527