Reaction of 1-substituted pyrroles with N-fluorodibenzenesulfonimide: Effect of halogen on electrophilic substitution by addition-elimination

Michael De Rosa, Vijay Rai Marwaha

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The reaction of 1-substituted pyrroles (1-methyl, 1-ethyl and 1-phenyl) with N-fluorodibenzenesulfonimide (NFSi) gave N-(1-substituted 1H-pyrrol-2-yl)dibenzenesulfonimides as products by addition elimination. Defluorination of NFSi was the only competing reaction. In contrast the reaction of 1-t-butylpyrrole with NFSi gave a mixture of fluoropyrroles. This is attributed to a steric interaction between the t-butyl group and the phenyl groups on NFSi. N-Chlorodibenzenesulfonimide was found to dechlorinate under all conditions studied and it was not possible to compare its reactivity with that of NFSi. The results of this study support our hypothesis that the observation of addition-elimination in pyrroles is related to the π-electron donating ability of the halogen initially introduced into the ring.

Original languageEnglish (US)
Pages (from-to)979-983
Number of pages5
JournalHeterocycles
Volume37
Issue number2
DOIs
StatePublished - Mar 3 1994

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Pyrroles
Halogens
Substitution reactions
Observation
N-fluorodibenzenesulfonimide
Electrons

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

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title = "Reaction of 1-substituted pyrroles with N-fluorodibenzenesulfonimide: Effect of halogen on electrophilic substitution by addition-elimination",
abstract = "The reaction of 1-substituted pyrroles (1-methyl, 1-ethyl and 1-phenyl) with N-fluorodibenzenesulfonimide (NFSi) gave N-(1-substituted 1H-pyrrol-2-yl)dibenzenesulfonimides as products by addition elimination. Defluorination of NFSi was the only competing reaction. In contrast the reaction of 1-t-butylpyrrole with NFSi gave a mixture of fluoropyrroles. This is attributed to a steric interaction between the t-butyl group and the phenyl groups on NFSi. N-Chlorodibenzenesulfonimide was found to dechlorinate under all conditions studied and it was not possible to compare its reactivity with that of NFSi. The results of this study support our hypothesis that the observation of addition-elimination in pyrroles is related to the π-electron donating ability of the halogen initially introduced into the ring.",
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Reaction of 1-substituted pyrroles with N-fluorodibenzenesulfonimide : Effect of halogen on electrophilic substitution by addition-elimination. / De Rosa, Michael; Marwaha, Vijay Rai.

In: Heterocycles, Vol. 37, No. 2, 03.03.1994, p. 979-983.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Reaction of 1-substituted pyrroles with N-fluorodibenzenesulfonimide

T2 - Effect of halogen on electrophilic substitution by addition-elimination

AU - De Rosa, Michael

AU - Marwaha, Vijay Rai

PY - 1994/3/3

Y1 - 1994/3/3

N2 - The reaction of 1-substituted pyrroles (1-methyl, 1-ethyl and 1-phenyl) with N-fluorodibenzenesulfonimide (NFSi) gave N-(1-substituted 1H-pyrrol-2-yl)dibenzenesulfonimides as products by addition elimination. Defluorination of NFSi was the only competing reaction. In contrast the reaction of 1-t-butylpyrrole with NFSi gave a mixture of fluoropyrroles. This is attributed to a steric interaction between the t-butyl group and the phenyl groups on NFSi. N-Chlorodibenzenesulfonimide was found to dechlorinate under all conditions studied and it was not possible to compare its reactivity with that of NFSi. The results of this study support our hypothesis that the observation of addition-elimination in pyrroles is related to the π-electron donating ability of the halogen initially introduced into the ring.

AB - The reaction of 1-substituted pyrroles (1-methyl, 1-ethyl and 1-phenyl) with N-fluorodibenzenesulfonimide (NFSi) gave N-(1-substituted 1H-pyrrol-2-yl)dibenzenesulfonimides as products by addition elimination. Defluorination of NFSi was the only competing reaction. In contrast the reaction of 1-t-butylpyrrole with NFSi gave a mixture of fluoropyrroles. This is attributed to a steric interaction between the t-butyl group and the phenyl groups on NFSi. N-Chlorodibenzenesulfonimide was found to dechlorinate under all conditions studied and it was not possible to compare its reactivity with that of NFSi. The results of this study support our hypothesis that the observation of addition-elimination in pyrroles is related to the π-electron donating ability of the halogen initially introduced into the ring.

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