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

doi:10.3987/R-1986-05-1311

A new mechanism (S_Ei) for electrophilic substitution in indoles. Chlorination of indoles with sodium hypochlorite by competitive S_E2 and S_Ei mechanisms

Michael De Rosa
, Angela Cuenca
, Maria Raquel Fernandez

Penn State Brandywine

Research output: Contribution to journal › Article › peer-review

4 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 S_Ei 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 S_E2 reaction to give 3-chloroindoles which were then converted to their N-chloro derivatives with excess NaOCl.

Original language	English (US)
Pages (from-to)	1311-1318
Number of pages	8
Journal	Heterocycles
Volume	24
Issue number	5
DOIs	https://doi.org/10.3987/R-1986-05-1311
State	Published - May 1 1986

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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

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.",

author = "\{De Rosa\}, Michael and Angela Cuenca and Fernandez, \{Maria Raquel\}",

year = "1986",

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doi = "10.3987/R-1986-05-1311",

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T1 - A new mechanism (SEi) for electrophilic substitution in indoles. Chlorination of indoles with sodium hypochlorite by competitive SE2 and SEi mechanisms

AU - De Rosa, Michael

AU - Cuenca, Angela

AU - Fernandez, Maria Raquel

PY - 1986/5/1

Y1 - 1986/5/1

N2 - 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.

AB - 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.

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DO - 10.3987/R-1986-05-1311

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SN - 0385-5414

VL - 24

SP - 1311

EP - 1318

JO - Heterocycles

JF - Heterocycles

IS - 5

ER -

A new mechanism (S_Ei) for electrophilic substitution in indoles. Chlorination of indoles with sodium hypochlorite by competitive S_E2 and S_Ei mechanisms

Abstract

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