Cytotoxic compounds. Part XVIII. Some 2-aryl-2-(arylthio)ethanols, 1-aryl-2-(arylthio)ethanols, and their methanesulphonates

Abstract

The reactions of sodium benzenethiolate with styrene oxide, with p-methoxystyrene oxide, and with p-nitrostyrene oxide each gave a mixture of the corresponding 2-aryl-2-(phenylthio)ethanol and 1-aryl-2-(phenylthio)ethanol, in the proportions 1 : 1, 4 : 1, and 1 : 2, respectively, illustrating the effect of the substituent on the stability of the benzylic carbonium ion responsible for the formation of the primary alcohols.

Methanesulphonates were prepared from all the primary alcohols, and from 1-(p-nitrophenyl)-2-(phenylthio)ethanol and 2-(2,4-dinitrophenylthio)-1-phenylethanol, but only chlorides could be obtained from 1-phenyl-2-(phenylthio)ethanol and 1-(p-methoxyphenyl)-2-(phenylthio)ethanol in their reactions with methanesulphonyl chloride. ¹H N.m.r. spectra of all these compounds, and of the acetates and methyl ethers, show characteristic differences between the primary and the secondary series.