Solvolyse von Toluolsulfonsäureestern XXVI : Neoisomenthol

Abstract

The unusually rapid course of the methanolysis of neoisomenthyltosylate gives partially racemised Δ³-menthene, Δ^4,8- menthene, the methylethers of both tertiary menthanols-(4) and that of isomenthol. The proportions of the amounts of reaction products are different from the ones found with neomenthyltosylate. This fact and especially the higher degree of racemization of Δ³-menthene can be explained by the participation of the tertiary hydrogen near the C⁴ of the neoisomenthyltosylate. The higher rate of solvolysis is due not only to this participation but also to the increase in the mobility of the cyclohexane ring. This mobility is also responsible for the strong dependence of the optical rotation of the neoisomenthol from the solvent.