Elimination from Diastereoisomeric Methyl 3-Acetoxy-2-halogeno- and 2,3-Dihalogeno-3-phenylpropanoates

CABALEIRO, M. C. ; GARAY, R. O.

JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2 (2001)

RSC

Lugar: Londres; Año: 1987 p. 1473 - 1476

1472-779X

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