Effect of N-chloro Structure and 1-substituent on (σ-substitution (Addition-Elimination) in Pyrroles

Michael De Rosa, Gustavo Cabrera Nieto, Fernando Ferrer Gago

Research output: Contribution to journalArticle

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Abstract

1-Methylpyrrole was reacted with a number of different types of N-chloro derivatives, and (σ-substitution was observed only with N-chloroimides. It is proposed that there is a qualitative relationship between the pKaof the N-chloro precursor and the reaction path. The reaction of 1-substituted pyrroles (CH3, C6H5, C6H6CH2, CH3CO0, (CH3)3C, CH2—CHCH2, (C6H6)3C) with N-chlorosuccinimide in CHCl3/NaHCO3indicated that (σ-substitution was very sensitive to electronic factors, e.g. no reaction was observed with 1-acetylpyrrole. It was not as sensitive to steric effects, and only with 1-tritylpyrrole was σ-substitution not observed. Only chlorination was observed with pyrrole itself.

Original languageEnglish (US)
Pages (from-to)5347-5350
Number of pages4
JournalJournal of Organic Chemistry
Volume54
Issue number22
DOIs
StatePublished - Oct 1 1989

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Pyrroles
Substitution reactions
Chlorination
Derivatives

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

De Rosa, Michael ; Nieto, Gustavo Cabrera ; Gago, Fernando Ferrer. / Effect of N-chloro Structure and 1-substituent on (σ-substitution (Addition-Elimination) in Pyrroles. In: Journal of Organic Chemistry. 1989 ; Vol. 54, No. 22. pp. 5347-5350.
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abstract = "1-Methylpyrrole was reacted with a number of different types of N-chloro derivatives, and (σ-substitution was observed only with N-chloroimides. It is proposed that there is a qualitative relationship between the pKaof the N-chloro precursor and the reaction path. The reaction of 1-substituted pyrroles (CH3, C6H5, C6H6CH2, CH3CO0, (CH3)3C, CH2—CHCH2, (C6H6)3C) with N-chlorosuccinimide in CHCl3/NaHCO3indicated that (σ-substitution was very sensitive to electronic factors, e.g. no reaction was observed with 1-acetylpyrrole. It was not as sensitive to steric effects, and only with 1-tritylpyrrole was σ-substitution not observed. Only chlorination was observed with pyrrole itself.",
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Effect of N-chloro Structure and 1-substituent on (σ-substitution (Addition-Elimination) in Pyrroles. / De Rosa, Michael; Nieto, Gustavo Cabrera; Gago, Fernando Ferrer.

In: Journal of Organic Chemistry, Vol. 54, No. 22, 01.10.1989, p. 5347-5350.

Research output: Contribution to journalArticle

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AB - 1-Methylpyrrole was reacted with a number of different types of N-chloro derivatives, and (σ-substitution was observed only with N-chloroimides. It is proposed that there is a qualitative relationship between the pKaof the N-chloro precursor and the reaction path. The reaction of 1-substituted pyrroles (CH3, C6H5, C6H6CH2, CH3CO0, (CH3)3C, CH2—CHCH2, (C6H6)3C) with N-chlorosuccinimide in CHCl3/NaHCO3indicated that (σ-substitution was very sensitive to electronic factors, e.g. no reaction was observed with 1-acetylpyrrole. It was not as sensitive to steric effects, and only with 1-tritylpyrrole was σ-substitution not observed. Only chlorination was observed with pyrrole itself.

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