Nitroaromatic bis(2-hydroxyethyl)dithioacetals and oxathioacetals using 2-mercaptoethanol in the presence of chlorosilanes

Abstract

Thioacetalization of the nitrobenzaldehydes with 2-mercaptoethanol is easily carried out in the presence of TMSCl and dichlorodimethylsilane without heating and using of additional solvent. The reaction direction is defined by the reagents ratio and led to formation of bis(2-hydroxyethyl)dithioacetals (yield 76-91%) or 1,3-oxathiolanes (yield 76-91%). Bis(2-hydroxyethyl)dithioacetals are easily transformed in the corresponding 1,3-oxathiolanes at long storage without heating or influence of catalysts, and also under electronic and chemical ionization.