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Reactivities of isomeric (1-dimethylaminovinyl)pyridines. Reaction with sulfene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown by means of quantum-chemical calculations (MINDO/3) and data from the 13C NMR and photoelectron (PE) spectra that a weak interaction between the enamine fragment and the heteroring, which deviates from its plane, exists in pyridyl enamines. The reaction of (1-dimethylaminovinyl)pyridines with sulfene leads to mixtures of 3-dimethylamino-3-pyridylthietane 1,1-dioxide (80%) and the corresponding methylsulfonyl ketone, the yield of which decreases as the acceptor character of the aromatic ring increases (α-Py < γ-Py §< β-Py < Ph). The structures of the enamines and the products of their reaction with sulfene were proved by IR, UV, and PMR spectroscopy, mass spectrometry, and the results of elementary analysis.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    L. N. Koikov, P. B. Terent'ev, I. P. Gloriozov, V. N. Torocheshnikov, V. N. Baidin & Yu. G. Bundel

  2. Scientific-Research Institute of Chemistry, A. A. Zhdanov Leningrad State University, 199164, Leningrad

    L. N. Koikov, P. B. Terent'ev, I. P. Gloriozov, V. N. Torocheshnikov, V. N. Baidin & Yu. G. Bundel

Authors
  1. L. N. Koikov
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  2. P. B. Terent'ev
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  3. I. P. Gloriozov
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  4. V. N. Torocheshnikov
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  5. V. N. Baidin
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  6. Yu. G. Bundel
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 643–650, May, 1983.

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Koikov, L.N., Terent'ev, P.B., Gloriozov, I.P. et al. Reactivities of isomeric (1-dimethylaminovinyl)pyridines. Reaction with sulfene. Chem Heterocycl Compd 19, 518–524 (1983). https://doi.org/10.1007/BF00514462

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  • DOI: https://doi.org/10.1007/BF00514462

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