Abstract 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 SN 2 and borderline SN 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 ...
