The reactions of a number of primary amines with a mono- and a tri-substituted epoxide have been examined. The results indicate that the presence of water has a strong reaction-accelerating effect for both heterocycles, and product studies have led to the isolation of secondary and tertiary amino-alcohols. Reactions of some amines possessing a weakly acidic group in the β-position proceeded anomalously rapidly, even under dry conditions, and it is suggested that these represent new examples of electrophilic anchimeric assistance.
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Burfield et al. (1977) studied this question.