Unusual reactivity of the 2H-thiopyran anion in alkylation with t-butyl bromide and cyclohexyl bromide
Abstract
The anion of 2H-thiopyran (2) reacts with t-butyl bromide and cyclohexyl bromide in liquid ammonia to give 2-t-bytyl-2H-thiopyran and a mixture of 2-cyclohexyl-2H-thiopyran and 4-cyclohexyl-4H-thiopyran in 53 and 82% yield, respectively.