Abstract
The reactions of 1,2-epoxypropane (I) and 2-methyl-2,3-epoxypentane (II) with various primary and secondary amines and with hexahydrophthalic anhydride in the presence of hydroxylic catalysts have been studied. The direction of ring opening of the epoxides on reaction with the amines is unaltered by the presence of phenol as catalyst, and involves attack at the least substituted carbon atom of the epoxide ring. The structures of the piperidino adducts ( viz. IV and V) derived from the phenol-catalysed reaction of piperidine with I and II, respectively, were proved by unambiguous syntheses of IV and V by the interaction of the corresponding chlorhydrin with piperidine. With hexahydrophthalic anhydride in the presence of water, I gave a low molecular weight polymeric ester whereas II afforded mainly a diadduct derived from the reaction of two molecules of II with one molecule of the anhydride. Reaction mechanisms are discussed briefly.
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