Issue 4, 1981

Electrophilic ipso-substitutions. Part 1. Reaction of 3-substituted indoles with nitronium and nitrosonium ions

Abstract

3-Substituted indoles react with nitronium and nitrosonium ions to yield 3-nitroindole. In both cases the reaction was interpreted as an electrophilic ipso-substitution. The reaction mechanism is interpreted by hypothesizing the formation of a σ-complex-like intermediate, which is some cases is preceded by an electron-transfer process. An order for the leaving abilities of the different electrofugal groups is discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1981, 628-632

Electrophilic ipso-substitutions. Part 1. Reaction of 3-substituted indoles with nitronium and nitrosonium ions

M. Colonna, L. Greci and M. Poloni, J. Chem. Soc., Perkin Trans. 2, 1981, 628 DOI: 10.1039/P29810000628

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