Abstract
Thermal rearrangement of diastereomeric 7-vinylnorcaradienes 2 and 3 resulted in the formation of three products, two of which were derived from the vinylcyclopropane-cyclopentene rearrangement and the third from the Cope rearrangement. Almost identical product ratios from 2 and 3 suggested the existence of a common biradical as an intermediacy. The kinetic versus thermodynamic control of the rearrangement was achieved by the choice of the substituent (X) in norcaradienes 9.
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