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Reactions of arylsulfonyl compounds with an excess of an organolithium reagent 14. The action of organolithium reagents on tert-butyl pyridinyl sulfones

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The tert-butyl sulfonyl groups in tert-butyl pyridin-2-yl and pyridin-4-yl sulfones are replaced by butyl groups under the action of BuLi predominantly by the AEn mechanism, and in the case of tert-butyl pryidin-4-yl sulfone also partially by the “lithioaryne” mechanisms through the intermediate formation of 5-lithio-3,4-dehydropyridine.

  2. 2.

    The replacement of the sulfonyl group in tert-butyl pyridin-4-yl sulfone under the action of DIPA-Li takes place by the “lithioaryne” mechanism.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    F. M. Stoyanovich, Ya. L. Gol'dfarb, M. A. Marakatkina & R. G. Karpenko

Authors
  1. F. M. Stoyanovich
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  2. Ya. L. Gol'dfarb
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  3. M. A. Marakatkina
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  4. R. G. Karpenko
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Additional information

For Communication 13, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2767–2771, December, 1978.

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Stoyanovich, F.M., Gol'dfarb, Y.L., Marakatkina, M.A. et al. Reactions of arylsulfonyl compounds with an excess of an organolithium reagent 14. The action of organolithium reagents on tert-butyl pyridinyl sulfones. Russ Chem Bull 27, 2469–2473 (1978). https://doi.org/10.1007/BF00941098

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  • DOI: https://doi.org/10.1007/BF00941098

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