synthesis of 1-Phenyl -1, 2-Cyclohexadiene and 1-(2-Bromocyclohex-2-En-1-Yl)Benzene and Wurtz-Like Condensation Products in the reaction of 1-(2,3-Dibromocyclohex-1-En-1-Yl) Benzene with Zinc

Abstract

The base-catalysed elimination of 1-(2-bromocyclohex-2-en-1-yl)benzene 1 and the zinc-catalysed elimination of 1-(2,3-dibromocyclohex-1-en-1-yl)benzene 9 have been used for the synthesis of 1-phenyl-1,2-cyclohexadiene 2; reaction of 9 with zinc in THF resulted in the formation of two isomeric Wurtz-like condensation products 3 and 4, but the reaction of 1 with t-BuOK gave the allene 2.