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Nitroylides 3. Synthesis and reactions of trinitromethylsulfonium salts

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

Conclusions

  1. 1.

    By nitration of (CH3)2S+-C(NO2)2 − with mixed HNO3-H2SO4 or NO2 + BF4 − we have prepared the first onium compound with three nitro groups on theα-carbon.

  2. 2.

    Trinitromethylsulfonium salts are easily cleaved at the S-CNO 2 bond by nucleophiles (Cl−, Br−, Ph¯S) and by electrophiles (halogens, N-haloimides, PhSCl, N2O4) to form the trinitromethyl derivatives, HalC(NO2)3, PhSC(NO2)3, and C(NO2)4.

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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

    S. A. Shevelev, V. V. Semenov & A. A. Fainzil'berg

Authors
  1. S. A. Shevelev
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  2. V. V. Semenov
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  3. A. A. Fainzil'berg
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Additional information

Preliminary communication [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2530–2535, November, 1977.

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Shevelev, S.A., Semenov, V.V. & Fainzil'berg, A.A. Nitroylides 3. Synthesis and reactions of trinitromethylsulfonium salts. Russ Chem Bull 26, 2345–2350 (1977). https://doi.org/10.1007/BF00958723

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  • DOI: https://doi.org/10.1007/BF00958723

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