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Nitro ylides. 7. Synthesis and some reactions of alkyl-substituted selenonium nitro ylides

  • V. V. Semenov
  • L. G. Mel'nikova
  • S. A. Shevelev
  • A. A. Fainzil'berg
Organic Chemistry
  • 36 Downloads

Conclusions

  1. 1.

    Stable dialkylselenonium nitro ylides have been synthesized.

     
  2. 2.

    In reactions with strong electrophilic reagents (halogens, hydrogen halides, and N-halo imides), the dialkylselenonium nitro ylides behave like their diphenylselenonium analogs: cleavage of the intermediate selenonium salt by the counterion and by a second molecule of electrophile takes place exclusively at the\(Se--C_{NO_2 } \) bond.

     
  3. 3.

    A study has been made of the ability of iodonium nitro ylides to transfer a nitromethylene fragment to sulfides and selenides to form the corresponding sulfonium and selenonium ylides.

     
  4. 4.

    The feature distinguishing the dialkylselenonium nitro ylides from their diaryl analogs is their ability to undergo a transylidation reaction with thiourea.

     

Keywords

Hydrogen Sulfonium Sulfide Thiourea Halide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • V. V. Semenov
    • 1
  • L. G. Mel'nikova
    • 1
  • S. A. Shevelev
    • 1
  • A. A. Fainzil'berg
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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