Replacement of nitro group of alkoxy group in 6-nitro-2,9-dioxa-1-azabicyclo[4.3.0]-nonane derivatives

  • I. E. Chlenov
  • I. M. Petrova
  • V. M. Shitkin
  • V. A. Tartakovskii
Brief Communications
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Conclusions

  1. 1.

    The reaction of 6-nitro-2,9-dioxa-1-azabicyclo[4.3.0]nonane derivatives with alcohols and alcoholates leads to remplacement of the nitro group by the corresponding alkoxy group.

     
  2. 2.

    The reaction proceeds with either a complete (for the case of the alcoholates) or predominant (for the case of alcohols) inversion of the configuration at the substitution center.

     
  3. 3.

    The reaction proceeds via the intermediately formed bicyclic immonium cation.

     

Keywords

Alcohol Nonane Nitro Group Alkoxy Group Nonane Derivative 

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Literature cited

  1. 1.
    I. E. Chlenov, I. M. Petrova, V. M. Shitkin, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 1365.Google Scholar
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    L. G. Vorontsova, V. M. Shitkin, O. S. Chizhov, I. M. Petrova, I. E. Chlenov, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 810.Google Scholar
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    V. M. Shitkin, V. I. Khudak, I. E. Chlenov, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 1908.Google Scholar
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    R. Grée and R. Carrié, Tetrahedron Lett.,1972, 2987.Google Scholar
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    N. Gravitz and W. P. Jencks, J. Am. Chem. Soc.,96, 489 (1974).Google Scholar

Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • I. E. Chlenov
    • 1
  • I. M. Petrova
    • 1
  • V. M. Shitkin
    • 1
  • V. A. Tartakovskii
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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