Regioselectivity of the acidolysis of 2-(chloromethyl)oxirane with aromatic acids in the presence of organic bases

Regioselectivity of the reaction of 2-(chloromethyl)oxirane with aromatic acids in the presence of tertiary amines and tetraalkylammonium halides has been studied. Opening of the oxirane ring follows simultaneously S N 2 and borderline S N 2 mechanisms. The regioselectivity of the acidolysis of substituted oxiranes is determined by acid-base properties of the reactants and catalysts and steric factor. The regioselectivity increases as the contribution of the S N 2 mechanism increases.