Nucleophilic substitution in iodonium derivatives of indole
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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.
KeywordsMass Spectrum Organic Chemistry Indole Halide Halogen
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- 1.H. Wiehe (editor), Advances in the Chemistry of Acetylenic Compounds [Russian translation], Khimiya, Moscow (1973), p. 247.Google Scholar
- 2.B. Ya. Karele, L. É. Treigute, S. V. Kalnin', I. P. Grinberga, and O. Ya. Neiland, Khim. Geterotsikl. Soedin., No. 2, 214 (1974).Google Scholar
- 3.L. G. Yudin, V. A. Budylin, A. N. Kost, and V. I. Minkin, Dokl. Akad. Nauk SSSR, 176, 1096 (1967).Google Scholar
- 4.J. C. Powers, J. Org. Chem., 31, 2627 (1966).Google Scholar
- 5.R. Weissberger, Ber., 46, 651 (1913).Google Scholar