Catalytic activity of tertiary amines with antisymbatic change of basic and nucleophilic properties in the chloroxypropylation reaction of acetic acid.

The kinetic dependence of the reaction of (chloromethyl)oxirane ring-opening by acetic acid in the presence of tertiary amines RN and RNMe has been studied. The orders of reaction with respect to acid and catalyst have been determined. The nucleophilicity of amines used has been measured in the quaternization reaction of RN and RNMe by benzyl chloride (Menshutkin reaction). On the basis of correlations 'amines structure-catalytic activity', it has been shown that amines act as nucleophiles in this reaction. [ABSTRACT FROM AUTHOR]