Dehydroacetoxylation and acetate transesterification in the reactions of erythro-and threo-methyl 3-(substituted acetoxy)-2-halogeno-3-phenylpropanoates with triethylamine
Abstract
The response of the rate of triethylamine-induced dehydroacetoxylation of methyl threo-3-acetoxy-2-halogeno-3-phenylpropanoate to the influence of substituents in the leaving group points to a change in mechanism from (E1 cB)I to a concerted process of the carbanion type. On the other hand, the erythro-isomers seem to undergo elimination exclusively through a carbanionic pathway. The effect of the acetoxy substituents upon the competitive transesterification is discussed.