Journal of the American Chemical Society

Deuterium isotope effects for migrating and nonmigrating groups in the solvolysis of neopentyl-type esters

VJ Shiner Jr, JJ Tai

Index: Shiner, V. J.; Tai, Jimmy J. Journal of the American Chemical Society, 1981 , vol. 103, # 2 p. 436 - 442

Full Text: HTML

Citation Number: 23

Abstract

Abstract: a-and y-deuterium rate effects on the solvolysis of (1-methylcyclohexyl) methyl,(1- methylcyclopentyl) methyl, and (1-methylcyclobutyl) methyl sulfonate esters have been measured and the solvolysis products examined by* H NMR spectroscopy. The results indicate that the products of the solvolysis of all these sulfonate esters are predominantly (298%) rearranged. In the solvolysis of (1-methylcyclohexyl) methyl triflate, rearranged ...