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

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

doi:10.1007/BF00957069

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

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

Research output: Contribution to journal › Article › peer-review

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Abstract

1. α-Piperidino- and α-morpholinocrotonaldehydes react with HCl, CF₃COOH, and CCl₃COOH to give enammonium ion salts exclusively. 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. The relative rates of hydrolysis of α-piperidino- and α-morpholinocrotonaldehydes, leading to the formation of ethylglyoxal and free amine, were also determined.

Original language	English
Pages (from-to)	957-961
Number of pages	5
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	37
Issue number	5
DOIs	https://doi.org/10.1007/BF00957069
State	Published - 1 Jan 1988
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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Keiko, N. A., Rulev, A. Y., Kalikhman, I. D., Shergina, N. I., Sherstyannikova, L. V., & Voronkov, M. G. (1988). Protonation regioselectivity and rates of hydrolysis of α-piperidino-and α-morpholinocrotonaldehydes, and E,Z-isomerization of their enammonium salts. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 37(5), 957-961. https://doi.org/10.1007/BF00957069

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

abstract = "1. α-Piperidino- and α-morpholinocrotonaldehydes react with HCl, CF3COOH, and CCl3COOH to give enammonium ion salts exclusively. 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. The relative rates of hydrolysis of α-piperidino- and α-morpholinocrotonaldehydes, leading to the formation of ethylglyoxal and free amine, were also determined.",

author = "Keiko, \{N. A.\} and Rulev, \{A. Yu\} and Kalikhman, \{I. D.\} and Shergina, \{N. I.\} and Sherstyannikova, \{L. V.\} and Voronkov, \{M. G.\}",

year = "1988",

month = jan,

day = "1",

doi = "10.1007/BF00957069",

language = "English",

volume = "37",

pages = "957--961",

journal = "Bulletin of the Academy of Sciences of the USSR Division of Chemical Science",

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number = "5",

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Keiko, NA, Rulev, AY, Kalikhman, ID, Shergina, NI, Sherstyannikova, LV & Voronkov, MG 1988, 'Protonation regioselectivity and rates of hydrolysis of α-piperidino-and α-morpholinocrotonaldehydes, and E,Z-isomerization of their enammonium salts', Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, vol. 37, no. 5, pp. 957-961. https://doi.org/10.1007/BF00957069

Protonation regioselectivity and rates of hydrolysis of α-piperidino-and α-morpholinocrotonaldehydes, and E,Z-isomerization of their enammonium salts. / Keiko, N. A.; Rulev, A. Yu; Kalikhman, I. D. et al.
In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 37, No. 5, 01.01.1988, p. 957-961.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Protonation regioselectivity and rates of hydrolysis of α-piperidino-and α-morpholinocrotonaldehydes, and E,Z-isomerization of their enammonium salts

AU - Keiko, N. A.

AU - Rulev, A. Yu

AU - Kalikhman, I. D.

AU - Shergina, N. I.

AU - Sherstyannikova, L. V.

AU - Voronkov, M. G.

PY - 1988/1/1

Y1 - 1988/1/1

N2 - 1. α-Piperidino- and α-morpholinocrotonaldehydes react with HCl, CF3COOH, and CCl3COOH to give enammonium ion salts exclusively. 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. The relative rates of hydrolysis of α-piperidino- and α-morpholinocrotonaldehydes, leading to the formation of ethylglyoxal and free amine, were also determined.

AB - 1. α-Piperidino- and α-morpholinocrotonaldehydes react with HCl, CF3COOH, and CCl3COOH to give enammonium ion salts exclusively. 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. The relative rates of hydrolysis of α-piperidino- and α-morpholinocrotonaldehydes, leading to the formation of ethylglyoxal and free amine, were also determined.

UR - https://www.scopus.com/pages/publications/1342335125

U2 - 10.1007/BF00957069

DO - 10.1007/BF00957069

M3 - Article

AN - SCOPUS:1342335125

SN - 0568-5230

VL - 37

SP - 957

EP - 961

JO - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

JF - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

IS - 5

ER -

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

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