Redox-chain decomposition of hydroxylamine-O-sulphonic acid. A novel general source of nucleophilic radicals for the functionalization of heteroaromatic bases

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

Index: Citterio, Attilio; Gentile, Anna; Minisci, Francesco; Serravalle, Marco; Ventura, Susanna Journal of the Chemical Society, Chemical Communications, 1983 , # 16 p. 916 - 917

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Abstract

Protonated heteroaromatic bases react with formamide, N,N-dimethylformamide, cyclic ethers, and methanol in the presence of hydroxylamine-0-sulphonic acid and catalytic amounts of an iron(ii) salt to afford selective substitution by a redox chain process. ... The reaction of nucleophilic carbon-centred free-radicals with protonated heteroaromatic bases is one of the most significant substitution reactions of these substrates1 General free-radical sources for these ...