Sodium borohydride-carboxylic acid systems. Useful reagents for the alkylation of amines

P Marchini, G Liso, A Reho, F Liberatore…

Index: Marchini,P. et al. Journal of Organic Chemistry, 1975 , vol. 40, p. 3453 - 3456

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Citation Number: 129

Abstract

Our results demonstrate that hydrogen bromide addition to la and lb is regiospecific as well as stereospecific, whereas the addition of IC is nonregiospecific. The most convincing rationale of our results is depicted in Scheme I. We suggest that la or lb reacts with hydrogen bromide in a reversible process to form the corresponding unstable a-proton complex (2a or 2b), which readily breaks up to form a planar resonance stabilized a-allylic cation (3a or ...