Studies of the reactions of the anhydrosulphites of α-hydroxy-carboxylic acids. Part IV. Steric and electronic effects in the reaction with alcohols

Abstract

Factors affecting the rate of reaction of anhydrosulphites with alcohols have been studied. The nature of the C(5) substituent in the anhydrosulphite ring has been shown to exert a marked influence on the susceptibility of the C(4) carbonyl group to nucleophilic attack. The effect is attributed to changes in electron density consequent upon the electron-withdrawing, or -donating, power of the C(5) substituent. Variations in the structure of the attacking alcohol have been studied and shown to exert a less marked influence on the reaction. The relevance of these results to the effect of anhydrosulphite structure on its polymerisability is discussed.