Polar effects in free-radical reactions. Carbamoylation and. alpha.-N-amidoalkylation of heteroaromatic bases by amides and hydroxylamine-O-sulfonic acid

…, F Minisci, M Serravalle, S Ventura

Index: Citterio, Attilio; Gentile, Anna; Minisci, Francesco; Serravalle, Marco; Ventura, Susanna Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3364 - 3367

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Citation Number: 23

Abstract

The decomposition by Fe (I1) salt of hydroxylamine-0-sulfonic acid (HSA) in the presence of formamide, alkylformamides, and y-alkylacetamides provides the amino radical cation.+ NH3, which by hydrogen abstraction generates carbamoyl (CON<) and aN-amidoalkyl (CONC<) radicals. Both kinds of radicals have a clear-cut nucleophilic character and selectively attack protonated heteroaromatic bases, such as 4-methylquinoline or ...