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Replacement of nitro group by cyano group in 6-nitro-2,9-dioxa-1-azabicyclo[4.3.0]nonane series

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

Conclusions

  1. 1.

    When 6-nitro-2,9-dioxa-1-azabicyclo[4.3.0]nonane derivatives are treated with NaCN in either DMF or ethanol the nitro group is replaced by the cyano group, in which connection a mixture of two steric isomers is formed.

  2. 2.

    The replacement reaction proceeds via the step of prior ionization of the nitro group and subsequent attack of the intermediately formed immonium cation by the nucleophile.

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Literature cited

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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. 1365–1367, June, 1975.

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Chlenov, I.E., Petrova, I.M., Shitkin, V.M. et al. Replacement of nitro group by cyano group in 6-nitro-2,9-dioxa-1-azabicyclo[4.3.0]nonane series. Russ Chem Bull 24, 1258–1261 (1975). https://doi.org/10.1007/BF00922058

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  • DOI: https://doi.org/10.1007/BF00922058

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