Reaction of some alkenols with tetrachloromethane

The reaction of some alkenols with tetrachloromethane in the presence of a radical initiator was investigated. Regarding the effects of structural fea tures of the starting alkenol (number and position of methyl substituents a t the double bond and at the carbinol carbon atom, constitutional relations hip between the double bond and the hydroxyl group) there are two possible competing reactions: addition and cyclization. In the case of the simplest alkenols (without substituents and with a more remote double bond) addition occurs; mono- and disubstituted secondary and tertiary Delta (4)- and Delt a (5)-alkenols cyclize in high yields to give the corresponding cyclic ethe rs.