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Protonation regioselectivity and rates of hydrolysis of α-piperidino-and α-morpholinocrotonaldehydes, and E,Z-isomerization of their enammonium salts

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

Conclusions

  1. 1.

    α-Piperidino- and α-morpholinocrotonaldehydes react with HCl, CF3COOH, and CCl3COOH to give enammonium ion salts exclusively.

  2. 2.

    Based on NMR data, at −20°C E forms of the enammonium salts are formed first and gradually isomerized to the corresponding Z forms.

  3. 3.

    The relative rates of hydrolysis of α-piperidino- and α-morpholinocrotonaldehydes, leading to the formation of ethylglyoxal and free amine, were also determined.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    N. A. Keiko, A. Yu. Rulev, I. D. Kalikhman, N. I. Shergina, L. V. Sherstyannikova & M. G. Voronkov

Authors
  1. N. A. Keiko
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  2. A. Yu. Rulev
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  3. I. D. Kalikhman
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  4. N. I. Shergina
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  5. L. V. Sherstyannikova
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  6. M. G. Voronkov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1093–1098, May, 1988.

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Keiko, N.A., Rulev, A.Y., Kalikhman, I.D. et al. Protonation regioselectivity and rates of hydrolysis of α-piperidino-and α-morpholinocrotonaldehydes, and E,Z-isomerization of their enammonium salts. Russ Chem Bull 37, 957–961 (1988). https://doi.org/10.1007/BF00957069

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  • DOI: https://doi.org/10.1007/BF00957069

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