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Reaction of 3-indolylphenyliodonium betaine with electrophilic agents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Indolylphenyliodonium chloride and bromide, respectively, were obtained by the action of hydrochloric and hydrobromic acids on 3-indolylphenyliodonium betaine. Pyrolysis of the chloride leads to a mixture of 2- and 3-chloroindoles, while pyrolysis of the bromide leads only to 3-bromoindole. 1-Benzyl-2-chloroindole is obtained in the reaction of the betaine with benzyl chloride. The betaine reacts with dimethyl sulfate to give an iodonium salt, the reaction of which with lithium chloride and ammonium chloride leads to 1-methyl-2-chloroindole.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    V. A. Budylin, M. S. Ermolenko, F. A. Chugtai, P. A. Sharbatyan & A. N. Kost

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  1. V. A. Budylin
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  2. M. S. Ermolenko
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  3. F. A. Chugtai
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  4. P. A. Sharbatyan
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  5. A. N. Kost
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Additional information

Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1503–1505, November, 1981

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Budylin, V.A., Ermolenko, M.S., Chugtai, F.A. et al. Reaction of 3-indolylphenyliodonium betaine with electrophilic agents. Chem Heterocycl Compd 17, 1095–1097 (1981). https://doi.org/10.1007/BF00506459

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  • DOI: https://doi.org/10.1007/BF00506459

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