Peculiarities of nucleophilic substitution in indolyliodonium salts |
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Authors: | V. A. Budylin M. S. Ermolenko F. A. Chugtai A. N. Kost |
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Affiliation: | (1) M. V. Lomonosov Moscow State University, 117234 Moscow |
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Abstract: | 3-Indolylphenyliodonium trifluoroacetate reacts with ammonium bromide and lithium chloride and bromide to give 3-haloindoles. The reaction with ammonium chloride and tetrabutylammonium chloride leads to a mixture of 2- and 3-chloroindoles. The same mixture of chloroindoles is also formed by the action of lithium chloride but in the presence of 15-crown-5 ether. The course of the reaction is explained by ambident reaction of the cation of the iodonium salt.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1494–1496, November, 1981. |
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