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Nucleophilic substitution in iodonium derivatives of indole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Indolylphenyliodonium tosylate and trifluoroacetate were synthesized, and their reaction with halide anions was investigated. It is shown that the iodonium grouping is replaced by halogen in all cases. 3-Fluoroindole was synthesized for the first time. The mechanism of the reaction is discussed, and data from the mass spectra of the 3-haloindoles obtained are presented.

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Literature cited

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 933–935, July, 1978.

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Ermolenko, M.S., Budylin, V.A. & Kost, A.N. Nucleophilic substitution in iodonium derivatives of indole. Chem Heterocycl Compd 14, 752–754 (1978). https://doi.org/10.1007/BF00471643

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  • DOI: https://doi.org/10.1007/BF00471643

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