Regioselectivity of the acidolysis of 2-(chloromethyl)oxirane with aromatic acids in the presence of organic bases |
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| Authors: | M. A. Sinel’nikova E. N. Shved |
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| Affiliation: | 1. Donetsk National University, ul. Universitetskaya 24, Donetsk, 83001, Ukraine
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| 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 SN2 and borderline SN2 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 SN2 mechanism increases. |
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