Oxidative transformations of bicyclo[3,3,0]oct-7-ene-1-one

Abstract

Bicyclo[3,3,0]oct-7-en-1-one has been converted into cyclo-octane-1,5-dione derivatives by oxidative cleavage of the central double bond. Reaction of the unsaturated ketone with N-bromosuccinimide yielded a tribromide which by substitution reactions with silver acetate yielded mono- and di-acetoxy-derivatives. The structures of all products are portrayed. The synthesis of bicyclo[3,3,0]oct-7-ene-1,6-diol, starting from a monoacetate of the unsaturated ketone, has been achieved.