Reactions of 1-halocyclohexenes and 1-halo-4-methylcyclohexenes with potassium t- butoxide (t-BuOK) in dimethyl sulfoxide and tetrahydrofuran have been shown to take place by three competing dehydrohalogenation mechanisms. These are: dehydrohalogenation across the C1 C6 bond to give a cyclohexyne; dehydrohalogenation across the C1 C6 bond to give a 1, 2-cyclohexadiene: and prototropic rearrangement to the corresponding 3 ...