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Nitroylides 5. Synthesis and some reactions of iodonium nitroylides and α-nitro-substituted iodonium salts

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

Conclusions

  1. 1.

    We have synthesized iodonium nitroylides and examined some of their reactions.

  2. 2.

    Iodonium dinitroylides are cleaved by electrophiles such as halogens, N-halosuccimides, and PhSCl, giving halogen or thio derivatives of dinitromethane; the reaction with HCl forms dinitromethane.

  3. 3.

    We have prepared the firstα-nitro-substituted iodonium salts\([Ar\mathop {IC}\limits^ + H(NO_2 )_2 ]\) (A−=FSO −3 ,Cl−) and have shown that they are easily cleaved at the\(C_{NO_2 } \) bond by nucleophiles and electrophiles.

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Literature cited

  1. V. V. Semenov, S. A. Shevelev, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 2640.

  2. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 2621.

  3. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 711.

  4. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 2032.

  5. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1977, 139.

  6. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1977, 2530.

  7. S. A. Shevelev, V. V. Semenov, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 1091.

  8. O. Ya. Neiland and G. Ya. Vanag, Dokl. Akad. Nauk SSSR,141, 872 (1961).

    Google Scholar 

  9. Y. Hayasi, T. Okada, and M. Kawanisi, Bull. Chem. Soc. Jpn.,43, 2506 (1970).

    Google Scholar 

  10. W. A. Sheppard and O. W. Webster, J. Am. Chem. Soc.,95, 2695 (1973).

    Google Scholar 

  11. V. V. Semenov and S. A. Shevelev, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 2355.

  12. I. Gosney and D. Lloyd, Tetrahedron,29, 1697 (1973).

    Google Scholar 

  13. O. Ya. Neiland and B. Ya. Karele, Zh. Org. Khim.,7, 1611 (1971).

    Google Scholar 

  14. Methoden der Organischen Chemie (Houben-Weyl), Stuttgart,5/4, 670 (1960).

    Google Scholar 

  15. H. J. Lucas, E. R. Kennedy, and M. W. Formo, Org. Synth., Coll. Vol. 3, 483 (1955).

    Google Scholar 

  16. V. I. Erashko, A. V. Sultanov, and S. A. Shevelev, and A. A. Fainzil'berg, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 350.

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Authors and Affiliations

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

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

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

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2348–2354, October, 1978.

Preliminary communication [1].

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Semenov, V.V., Shevelev, S.A. & Fainzil'berg, A.A. Nitroylides 5. Synthesis and some reactions of iodonium nitroylides and α-nitro-substituted iodonium salts. Russ Chem Bull 27, 2080–2086 (1978). https://doi.org/10.1007/BF00946532

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  • DOI: https://doi.org/10.1007/BF00946532

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