Studies in the tricyclooctane series. V. Dehydrohalogenation of the Bis-dihalocarbene adducts of some methoxycyclohexadienes

Abstract

The bis-dichloro and bis-dibromo carbene adducts (1c-h) of 1-methoxy-, 1,4-dimethoxy- and 1,5-dimethoxy-cyclohexa-1,4-diene undergo regiospecific dehydrohalogenation by strong base to the 4,8,8- trihalomethoxybicyclo[5,1,0]octa-2,4-dienes (7c-h), in contrast to the 1,7-dimethoxytricyclooctane(1i) and its methyl derivatives (1j-m), which are unchanged. The dienes (7c-h) are resistant to further dehydrohalogenation.