Pyrroles from ketoximes and acetylene. 19. Regioselectivity of the reaction of alkyl benzyl ketoximes with acetylene

B. A. Trofimov; S. E. Korostova; L. N. Sobenina; A. I. Mikhaleva; V. M. Bzhezovskii; M. V. Sigalov; A. A. Atavin

doi:10.1007/BF00512958

Pyrroles from ketoximes and acetylene. 19. Regioselectivity of the reaction of alkyl benzyl ketoximes with acetylene

B. A. Trofimov, S. E. Korostova, L. N. Sobenina, A. I. Mikhaleva, V. M. Bzhezovskii, M. V. Sigalov, A. A. Atavin

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

Abstract

Alkyl benzyl ketoximes react with acetylene at 60-150 °C in MOH-dimethyl sulfoxide (M = Li, K) primarily by means of the methylene group of the benzyl grouping, which is primarily anti-oriented with respect to the hydroxy group, to give 2-alkyl-3-phenylpyrroles in greater than 70% yields. The specific participation of the antimethylene group in the construction of a pyrrole ring constitutes evidence against mechanisms that include a [3,3]-sigmatropic shift in O-vinyl oximes. It follows from the results obtained that the reaction proceeds through an anti-dianion of the benzyl type stabilized by conjugation with the aromatic ring.

Original language	English
Pages (from-to)	148-152
Number of pages	5
Journal	Chemistry of Heterocyclic Compounds
Volume	18
Issue number	2
DOIs	https://doi.org/10.1007/BF00512958
State	Published - 1 Feb 1982
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Pyrroles from ketoximes and acetylene. 19. Regioselectivity of the reaction of alkyl benzyl ketoximes with acetylene",

abstract = "Alkyl benzyl ketoximes react with acetylene at 60-150 °C in MOH-dimethyl sulfoxide (M = Li, K) primarily by means of the methylene group of the benzyl grouping, which is primarily anti-oriented with respect to the hydroxy group, to give 2-alkyl-3-phenylpyrroles in greater than 70% yields. The specific participation of the antimethylene group in the construction of a pyrrole ring constitutes evidence against mechanisms that include a [3,3]-sigmatropic shift in O-vinyl oximes. It follows from the results obtained that the reaction proceeds through an anti-dianion of the benzyl type stabilized by conjugation with the aromatic ring.",

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AU - Trofimov, B. A.

AU - Korostova, S. E.

AU - Sobenina, L. N.

AU - Mikhaleva, A. I.

AU - Bzhezovskii, V. M.

AU - Sigalov, M. V.

AU - Atavin, A. A.

PY - 1982/2/1

Y1 - 1982/2/1

N2 - Alkyl benzyl ketoximes react with acetylene at 60-150 °C in MOH-dimethyl sulfoxide (M = Li, K) primarily by means of the methylene group of the benzyl grouping, which is primarily anti-oriented with respect to the hydroxy group, to give 2-alkyl-3-phenylpyrroles in greater than 70% yields. The specific participation of the antimethylene group in the construction of a pyrrole ring constitutes evidence against mechanisms that include a [3,3]-sigmatropic shift in O-vinyl oximes. It follows from the results obtained that the reaction proceeds through an anti-dianion of the benzyl type stabilized by conjugation with the aromatic ring.

AB - Alkyl benzyl ketoximes react with acetylene at 60-150 °C in MOH-dimethyl sulfoxide (M = Li, K) primarily by means of the methylene group of the benzyl grouping, which is primarily anti-oriented with respect to the hydroxy group, to give 2-alkyl-3-phenylpyrroles in greater than 70% yields. The specific participation of the antimethylene group in the construction of a pyrrole ring constitutes evidence against mechanisms that include a [3,3]-sigmatropic shift in O-vinyl oximes. It follows from the results obtained that the reaction proceeds through an anti-dianion of the benzyl type stabilized by conjugation with the aromatic ring.

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Pyrroles from ketoximes and acetylene. 19. Regioselectivity of the reaction of alkyl benzyl ketoximes with acetylene

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