Russian Journal of Organic Chemistry

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

MA Sinel'nikova, EN Shved

Index: Sinel'nikova; Shved Russian Journal of Organic Chemistry, 2014 , vol. 50, # 3 p. 332 - 336 Zh. Org. Khim., 2014 , vol. 50, # 3 p. 343 - 348,6

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Citation Number: 2

Abstract

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 ...