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Geminal systems. 16. Reactions of N-chloro-N-alkoxy-N-alkylamines with amines

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

Conclusions

The reactions of N-chloro-N-alkoxy-N-tert-alkylamines with amines are characterized by nucleophilic substitution at the nitrogen atom with formation of the corresponding N-alkoxyhydrazines which are stable in the case of ethyleneimine and pyridine; give diazenes as in the case of MeNH2, EtNH2, and Me2

or yield products of further transformations as in the case of NH3, Me2NH, and MeO(Me)NH. Nucleophilic substitution is repressed in the reaction with Et2NH and Et3 N by one-electron reduction with the formation of azoxy compounds.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    V. G. Shtamburg, V. F. Rudchenko, Sh. S. Nasibov, I. I. Chervin, A. P. Pleshkova & R. G. Kostyanovskii

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  1. V. G. Shtamburg
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  2. V. F. Rudchenko
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  3. Sh. S. Nasibov
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  4. I. I. Chervin
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  5. A. P. Pleshkova
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  6. R. G. Kostyanovskii
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Additional information

For Communication 15, see previous article [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2327–2334, October, 1981.

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Shtamburg, V.G., Rudchenko, V.F., Nasibov, S.S. et al. Geminal systems. 16. Reactions of N-chloro-N-alkoxy-N-alkylamines with amines. Russ Chem Bull 30, 1914–1920 (1981). https://doi.org/10.1007/BF00963422

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  • DOI: https://doi.org/10.1007/BF00963422

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