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The reaction of stable sulfonium ylides of dimedone with triphenylphosphine

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

Conclusions

  1. 1.

    Triphenylphosphine demethylates 2-(methylphenylsulfuranylidene)-5,5-dimethylcyclohexane-1, 3-dione to form methyltriphenylphosphonium 2-(phenylthio)-5,5-dimethylcyclohexane-1,3-dione (IV).

  2. 2.

    Compound (IV) readily undergoes anion-exchange reactions with NaBPh4, MeI, moist SO2 (gas), dry HCl, and Me2SO4.

  3. 3.

    Dimethyl- and dibenzylsulfonium ylides of dimedone are desulfurized and deoxygenated by triphenylphosphine.

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Authors and Affiliations

  1. A. M. Butlerov Chemical Institute, USSR

    B. A. Arbuzov, Yu. V. Belkin, N. A. Polezhaeva & T. V. Yudina

  2. V. I. Ul'yanov-Lenin Kazan' State University, USSR

    B. A. Arbuzov, Yu. V. Belkin, N. A. Polezhaeva & T. V. Yudina

Authors
  1. B. A. Arbuzov
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  2. Yu. V. Belkin
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  3. N. A. Polezhaeva
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  4. T. V. Yudina
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2086–2090, September, 1977.

We thank É. I. Gol'dfarb for recording the31P NMR spectra, R. G. Gainullina for recording the PMR spectra, and V. S. Vinogradova for assistance in discussing the UV spectra.

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Arbuzov, B.A., Belkin, Y.V., Polezhaeva, N.A. et al. The reaction of stable sulfonium ylides of dimedone with triphenylphosphine. Russ Chem Bull 26, 1930–1933 (1977). https://doi.org/10.1007/BF00924392

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  • DOI: https://doi.org/10.1007/BF00924392

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