Nucleophilic attacks on carbon–carbon double bonds. Part 24. Nucleophilic substitution of (E)- and (Z)-3-chloro-2-phenylpropenonitriles; comments on the work of Le Guillanton and Cariou

Abstract

The contradictions between the results and conclusions of Le Guillanton and Cariou and those of Rappoport and Topol in studies of the nucleophilic substitutionof 3-chloro-2-phenylpropenonitriles are discussed. A mechanism is suggested for the ‘racemisation’ reaction observed at high ethoxide ion concentrations. Methods for determining the configurations of the substitution products are evaluated.