α-HYDROXYALKYLATION OF HETEROAROMATIC BASES BY ALCOHOLS AND HYDROXYLAMINE-O-SULPHONIC ACID

Article abstract of DOI:10.1016/S0040-4020(01)96508-1

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 NH3⁺, is suggested and the factors affecting the yields of the homolytic substitution are discussed.