A new mechanism (SEi) for electrophilic substitution in indoles. Chlorination of indoles with sodium hypochlorite by competitive SE2 and SEi mechanisms

Michael De Rosa, Angela Cuenca, Maria Raquel Fernandez

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3 Scopus citations

Abstract

The chlorination of 5-substituted indoles (OCH3, CH3, Br, CN, N02) with NaOCl was studied. Mixtures of N-chloro- and N-chloro-3-chloro-indoles were formed, Indoles reacted with OCl- in a SEi process to give N-chloroindoles. This reaction was favored by substituents which increased the acidity of the indolic N-H. Indoles or their conjugate bases also reacted with HOCl in a SE2 reaction to give 3-chloroindoles which were then converted to their N-chloro derivatives with excess NaOCl.

Original languageEnglish (US)
Pages (from-to)1311-1318
Number of pages8
JournalHeterocycles
Volume24
Issue number5
DOIs
StatePublished - May 1 1986

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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