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Asymmetrical nonbridgehead nitrogen

9. Derivatives of 1-alkoxyaziridine-2-carboxylic acids

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

Conclusions

  1. 1.

    We have developed a synthesis of derivatives of N-alkoxyaziridine-2-carboxylic acids by reaction of alkoxyamines with the corresponding vicinal dibromides in acetonitrile in the presence of triethylamine.

  2. 2.

    We have demonstrated the high configurational stability (ΔG ≠inv =30–32 kcal/mole) and thermal stability of derivatives of 1-alkoxyaziridine-2-carboxylic acids.

  3. 3.

    We have separated by crystallization the geometric isomers (cis and trans invertomers) of 1-methoxyaziridine-2-carboxamide.

  4. 4.

    We have synthesized the first optically active 1-alkoxyaziridines with two or more asymmetric centers in the molecule. We have prepared pure diastereomers of N-[(S)-α-phenylethyl]- trans-1-methoxyaziridine-2-carboxamide.

  5. 5.

    We have observed the stereospecific trans animation of 1-alkoxyaziridine-2-carboxylic esters by sterically hindered amines.

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Authors and Affiliations

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

    R. G. Kostyanovskii, A. V. Prosyanik, V. I. Markov, I. A. Zon & A. E. Polyakov

Authors
  1. R. G. Kostyanovskii
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  2. A. V. Prosyanik
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  3. V. I. Markov
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  4. I. A. Zon
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  5. A. E. Polyakov
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Additional information

For Communication 8, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1559–1571, July, 1976.

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Kostyanovskii, R.G., Prosyanik, A.V., Markov, V.I. et al. Asymmetrical nonbridgehead nitrogen. Russ Chem Bull 25, 1481–1492 (1976). https://doi.org/10.1007/BF00920823

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  • DOI: https://doi.org/10.1007/BF00920823

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