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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See [1] for communication 18.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 193–198, February, 1982.
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Trofimov, B.A., Korostova, S.E., Sobenina, L.N. et al. Pyrroles from ketoximes and acetylene. 19. Regioselectivity of the reaction of alkyl benzyl ketoximes with acetylene. Chem Heterocycl Compd 18, 148–152 (1982). https://doi.org/10.1007/BF00512958
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DOI: https://doi.org/10.1007/BF00512958