Elimination from diastereoisomeric methyl 3-acetoxy-2-halogeno- and 2,3-dihalogeno-3-phenylpropanoates

Abstract

The rates of elimination of a number of erythro- and threo-PhCHYCXHCO₂Me in methanolic triethylamine have been measured. The kinetic evidence together with the stereochemical results suggest that elimination of the dihalogeno-compounds occurs by an (E1cB)_I process for the erythro-substrates and by a concerted pathway for the thero-isomers. In the case of the acetoxy derivatives the former mechanism seems to be operative for both diastereoisomers.