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

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

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.

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Literature cited

  1. I. E. Chlenov, I. M. Petrova, V. M. Shitkin, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 1365.

  2. I. E. Chlenov, I. M. Petrova, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 2644.

  3. 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.

  4. V. M. Shitkin, V. I. Khudak, I. E. Chlenov, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 1908.

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Authors and Affiliations

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

    I. E. Chlenov, I. M. Petrova, V. M. Shitkin & V. A. Tartakovskii

Authors
  1. I. E. Chlenov
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  2. I. M. Petrova
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  3. V. M. Shitkin
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  4. V. A. Tartakovskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1405–1408, June, 1976.

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Chlenov, I.E., Petrova, I.M., Shitkin, V.M. et al. Replacement of nitro group of alkoxy group in 6-nitro-2,9-dioxa-1-azabicyclo[4.3.0]-nonane derivatives. Russ Chem Bull 25, 1347–1350 (1976). https://doi.org/10.1007/BF00928094

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  • DOI: https://doi.org/10.1007/BF00928094

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