Substitutions by nucleophilic free radicals: A new general reaction of heteroaromatic bases
- 1 January 1990
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 27 (1) , 79-96
Abstract
The substitution of protonated heteroaromatic bases by nucleophilic carbon‐centered radicals has been developed as one of the most general reactions in the heterocyclic series; its great interest results from the fact that it reproduces most of the numerous aspects of the Friedel‐Crafts aromatic substitution, but with opposite reactivity and selectivity. The most recent developments, concerning the generation of free radicals by iodine and hydrogen abstraction and decarboxylation of carboxylic acids are particularly discussed. Some processes of high synthetic value were designed on the basis of the kinetic and thermodynamic features of all the elementary steps involved in complex but selective chain processes. New general procedures for the monosubstitution in the homolytic alkylation and acylation are reported and discussed.Keywords
This publication has 41 references indexed in Scilit:
- Preparation of monoacylpyrazinesJournal of Heterocyclic Chemistry, 1986
- Polar effects in free radical reactions. Induced decompositions of peroxo compounds in the substitution of heteroaromatic bases by nucleophilic radicalsJournal of the American Chemical Society, 1984
- Free-radical diazocoupling. A new general reaction of diazonium saltsThe Journal of Organic Chemistry, 1982
- Nucleophilic character of alkyl radicals. XIV. Homolytic δ‐aminoalkylation of protonated quinoxalineJournal of Heterocyclic Chemistry, 1976
- Nucleophilic character of acyl radicals. Absolute rate constant for the acylation of protonated benzothiazole by pivaloyl radicalJournal of the Chemical Society, Perkin Transactions 2, 1976
- Homolytic acylation of protonated pyridine and pyrazine derivativesJournal of the Chemical Society, Perkin Transactions 2, 1972
- Nucleophilic character of acyl radicals. Homolytic acylation of quinoxalineJournal of the Chemical Society C: Organic, 1970
- Nucleophilic character of acyl radicals: a new selective type of aromatic acylationJournal of the Chemical Society D: Chemical Communications, 1969
- Positive Halogen Compounds. X. Solvent Effects in the Reactions of t-Butoxy RadicalsJournal of the American Chemical Society, 1964
- Tautomeric Equilibria. I. Substituted Pyridines and their 1-OxidesJournal of the American Chemical Society, 1955