Stereochemistry of elimination reactions of 2-chloro-1-phenylpropane in different solvent–base systems

Abstract

The stereochemistry of βelimination from DL-erythro-(I) and DL-threo-2-chloro-1-deuterio-1-phenyl propane (II) promoted by a variety of solvent-base combinations has been investigated. Elimination from (I) occurs by an anti-mechanism in EtOH–EtONa and in Bu^tOH–Bu^tOK–crown ether, whereas a small amount of syn-elimination (<6%) is observed in Bu^tOH–Bu^tOK. anti-Stereochemistry is always observed for eliminations from (II).