Nucleophilic substitution in iodonium derivatives of indole

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. © 1979 Plenum Publishing Corporation.