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Nitroylides

2. Reaction of sulfonium dinitroylides with electrophiles

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

Conclusions

  1. 1.

    Sulfonium dinitroylides\(R_2 \mathop S\limits^ + - C(NO_2 )_2^ - \) are cleaved at the\(S - C_{NO_2 } \) bond by electrophiles such as halogens (chlorine, bromine, bromine chloride), sulfuryl chloride, hydrogen halides (chloride and bromide), giving the corresponding di- or monohalodinitromethanes.

  2. 2.

    Phenylsulfenyl chloride reacts with\((CH_3 )_2 \mathop S\limits^ + - C(NO_2 )_2^ - \), forming dinitrobis(phenylthio)methane and dtnitrophenylthiomethane.

  3. 3.

    Compounds containing a positive halogen (N-haloamides, N-chloroalkylnitramines, BrONO2, SO2FCl, CH3CO2C1) react with\((CH_3 )_2 \mathop S\limits^ + - C(NO_2 )_2^ - \) to give the corresponding dihalodinitromethanes.

  4. 4.

    Electrophiles (chlorine, bromine, phenylsulfenyl chloride) are capable of cleaving the\(S - C_{NO_2 } \) bond of dinitromethylsulfonium salts, forming the corresponding monosubstituted dinitromethane, ClCH(NO2)2, BrCH(NO2)2, and PhSCH(NO2)2. On the basis of our results we propose a scheme for the reaction of\((CH_3 )_2 \mathop S\limits^ + - C(NO_2 )_2^ - \) with phenylsulfenyl chloride and compounds containing a positive halogen.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 139–147, January, 1977.

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Shevelev, S.A., Semenov, V.V. & Fainzil'berg, A.A. Nitroylides. Russ Chem Bull 26, 120–125 (1977). https://doi.org/10.1007/BF00921507

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  • DOI: https://doi.org/10.1007/BF00921507

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