Molecules p. 1527 - 1543 (2014)
Update date:2022-08-03
Topics: NMR spectroscopy Flash column chromatography Hydrolysis Thermocouple
Leber, Phyllis A.
Nocket, Anthony J.
Hancock-Cerutti, William
Bemis, Christopher Y.
Khine, Wint Khant
Mohrbacher III, Joseph A.
Baldwin, John E.
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.
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