The acid catalysed hydrolysis of tetramethylethylene oxide

Abstract

The acid catalysed hydrolysis of tetramethylethylene oxide has been studied in perchloric acid solutions. In all cases examined, yields of pinacol were greater than 98%, while those of pinacolone were less than 1%. Comparison of these product ratios with the partitioning ratio of the kinetically free carbonium ion formed in the pinacol rearrangement indicates an A-2 mechanism for the hydrolysis. Preparative routes to tetramethylethylene oxide via tetramethylethylene bromhydrin or chlorhydrin, and via tetramethylethylene have been examined.