Electrophilic ipso-Substitutions. Part 1. Reaction of 3-Substituted Indoles with Nitronium and Nitrosonium Ions

DOI: 10.1039/P29810000628

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 628 - 632 (1981)

Update date:2022-08-05

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Authors:

Colonna, Martino

Greci, Lucedio

Poloni, Marino

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Article abstract of DOI:10.1039/P29810000628

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 ?-complex-like intermediate, wich is some cases is preceded by an electron-transfer process.An order for the leaving abilities of the different electrofugal groups is discussed.

Full text of DOI:10.1039/P29810000628

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