Studies in the tricyclooctane series. VI. Dehydrohalogenation of 8,8-dihalobicyclo[5,1,0]octa-2,4-dienes : Plausible intermediates in the tricyclooctane-styrene conversion

Abstract

The dehydrohalogenation of 8,8-dichloro- and 8,8-dibromo- bicyclo[5,1,0]octa-2,4-diene (4c,d)gives rise to the (E)- and (Z)-isomers of β-t-butoxystyrene (2c). Plausible pathways for the conversion are discussed and evidence in support of bicyclo[4,2,0]octa- 2,4-dienes as intermediates in the conversion is presented. The results support the intervention of halobicyclo[5,1,0]octa-2,4-dienes in the conversion of tetra- and tri-halo-cis-transoid-cis- tricyclo[5,1,0,0^3,5]octanes (1a-d) to styrenes(2a-c).