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Paper | Regular issue | Vol 36, No. 12, 1993, pp.2687-2696
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6459
A Facile, Convenient and Selective Homolytic Carbamolylation of Heteroaromatic Bases

Fausta Coppa, Francesca Fontana, Edoardo Lazzarini, and Francesco Minisci*

*Dipartimento di Chimica, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133 Milano, Italy


The oxidative decarboxylation of monoamides of oxalic acid provides carbamoyl radicals, which are useful for the selective arbamoylation of protonated heteroaromatic bases; this reaction represnets the first general and selective method for the N-alkyl or N-arylcarbamoylation of heteroaromatic bases. Compared to alkoxycarbonylation, this reaction is much more effective and selective, owing to more favourable polar and enthalpic effects. The importance of the steric effects is also emphasized.