Nucleophilic substitution of hydroxyl groups in 2-alkyl(aryl)thioethanols

Abstract

1. The reactions of 2-alkyl(aryl)thioethanols with HCl in hydrochloric acid, alcohols, and thiols under anhydrous conditions have been studied. It has been shown that selective replacement of the hydroxyl groups in these compounds by chlorine atoms and alkoxy, alkyl, and arylthio groups occurs under certain conditions under catalysis by strong mineral acids. 2. Several laws governing the acid-catalyzed nucleophilic substitution of hydroxyl groups in 2-alkyl(aryl)thioethanols have been revealed. In particular, an increase in the selectivity of the process with decreasing strength of the nucleophilic reagent has been established.