Radical-mediated transannulation reactions in humulene. A new synthesis of substituted bicyclo[6.3.0]undeca-4,9-dienes

Abstract

Treatment of the undeca-1,4,8-triene hydrocarbon humulene 1 with ethanethiol radicals results in a facile radical-mediated transannulation producing the sulfide 7 in 50% yield. The structure of 7 follows from its conversion into the bicyclo[6.3.0]undeca-4,9-diene 9 and from an X-ray crystal determination on the di-epoxide 10 derived from 9.