The mechanism of the pinacol-pinacone rearrangement. IV. Exchange and rearrangement with hydrogen isotopes

Abstract

The two hydroxyl atoms of pinacol exchange very rapidly and quantitatively with ³H₂O even at room temperature. The rate of the pinacol-pinacone rearrangement in 99.7 per cent. D₂O with unibasic acids at 100 °C is about 1.9 times faster than that obtained in ordinary water. Although these results conform with the generally accepted mechanism, some features are unexpected.