Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 6. A simple preparation of chlorohydrin benzoates from 1,2-and 1,3-glycols

Abstract

Treatment of 1,2-diols and of one 1,3-diol with the imidoyl chloride derived from dimethylbenzamide afforded, at room tempreature, in excellent yields and regiospecifically the corresponding chlorohydrin benzoates. The reaction is considered to proceed via the appropriate phenyl(dioxacycloalkylium) intermediate and is shown to involve inversion of configuration at the centre to which chlorine is attached. The ordinary Vilsmeier reagent from dimethylformamide gives diformates under the same conditions.