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.