Tetrahedron

α-Hydroxyalkylation of heteroaromatic bases by alcohols and hydroxylamine-O-sulphonic acid

A Citterio, A Gentile, F Minisci, M Serravalle, S Ventura

Index: Citterio, Attilio; Gentile, Anna; Minisci, Francesco; Serravalle, Marco; Ventura, Susanna Tetrahedron, 1985 , vol. 41, # 3 p. 617 - 620

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Citation Number: 11

Abstract

The homolytic decomposition of hydroxylamine-O-sulphonic acid in alcoholic solvents was investigated in the presence or absence of protonated heteroaromatic bases and Fe (II) salt. The addition of the α-hydroxyalkyl radicals to the base and their oxidation by Fe (III) salt to the corresponding alkyl cyanide were competitive processes. A redox chain process involving the amino radical cation, NH3t., is suggested and the factors affecting the yields ...