NMR spectra and structures of protonated 1-vinylpyrroles

M. V. Sigalov; E. Yu Shmidt; A. I. Mikhaleva; S. E. Korostova; I. M. Lazarev; B. A. Trofimov

doi:10.1007/BF00528634

NMR spectra and structures of protonated 1-vinylpyrroles

M. V. Sigalov, E. Yu Shmidt, A. I. Mikhaleva, S. E. Korostova, I. M. Lazarev, B. A. Trofimov

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

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Abstract

Stable 1-vinylpyrrolium fluorosulfonates were prepared by the reaction of 1-vinylpyrroles with excess HSO₃F at -50°C in CD₂Cl₂ and their ¹H and ¹³C NMR spectra were obtained. Despite its overall positive charge, the pyrrole ring remains an electron donor relative to the vinyl group. Delocalization of the positive charge onto substituents decreases in the order 2-heteroaryl > 2-aryl > 2-alkyl.

Original language	English
Pages (from-to)	40-48
Number of pages	9
Journal	Chemistry of Heterocyclic Compounds
Volume	29
Issue number	1
DOIs	https://doi.org/10.1007/BF00528634
State	Published - 1 Jan 1993
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "NMR spectra and structures of protonated 1-vinylpyrroles",

abstract = "Stable 1-vinylpyrrolium fluorosulfonates were prepared by the reaction of 1-vinylpyrroles with excess HSO3F at -50°C in CD2Cl2 and their 1H and 13C NMR spectra were obtained. Despite its overall positive charge, the pyrrole ring remains an electron donor relative to the vinyl group. Delocalization of the positive charge onto substituents decreases in the order 2-heteroaryl > 2-aryl > 2-alkyl.",

author = "Sigalov, {M. V.} and Shmidt, {E. Yu} and Mikhaleva, {A. I.} and Korostova, {S. E.} and Lazarev, {I. M.} and Trofimov, {B. A.}",

year = "1993",

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T1 - NMR spectra and structures of protonated 1-vinylpyrroles

AU - Sigalov, M. V.

AU - Shmidt, E. Yu

AU - Mikhaleva, A. I.

AU - Korostova, S. E.

AU - Lazarev, I. M.

AU - Trofimov, B. A.

PY - 1993/1/1

Y1 - 1993/1/1

N2 - Stable 1-vinylpyrrolium fluorosulfonates were prepared by the reaction of 1-vinylpyrroles with excess HSO3F at -50°C in CD2Cl2 and their 1H and 13C NMR spectra were obtained. Despite its overall positive charge, the pyrrole ring remains an electron donor relative to the vinyl group. Delocalization of the positive charge onto substituents decreases in the order 2-heteroaryl > 2-aryl > 2-alkyl.

AB - Stable 1-vinylpyrrolium fluorosulfonates were prepared by the reaction of 1-vinylpyrroles with excess HSO3F at -50°C in CD2Cl2 and their 1H and 13C NMR spectra were obtained. Despite its overall positive charge, the pyrrole ring remains an electron donor relative to the vinyl group. Delocalization of the positive charge onto substituents decreases in the order 2-heteroaryl > 2-aryl > 2-alkyl.

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JO - Chemistry of Heterocyclic Compounds

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IS - 1

ER -

NMR spectra and structures of protonated 1-vinylpyrroles

Abstract

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