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Reaction of Trichloromethylarenes with Pyridine: A Novel Synthesis of N-(4-Pyridyl)pyridinium Salts and Aromatic Aldehydes

Leonid Isaakovich Belen'kii 1
Leonid Isaakovich Belen'kii
, 
Igor Sergeyevich Poddubny 1
Igor Sergeyevich Poddubny
, 
Mikhail Mikhailovich Krayushkin 1
Mikhail Mikhailovich Krayushkin
10.1070/MC1993v003n03ABEH000240
Published 1993-06-30
Communication , Volume 3, Issue 3, 97-98
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Belen'kii L. I., Poddubny I. S., Krayushkin M. M. Reaction of Trichloromethylarenes with Pyridine: A Novel Synthesis of N-(4-Pyridyl)pyridinium Salts and Aromatic Aldehydes // Mendeleev Communications. 1993. Vol. 3. No. 3. pp. 97-98.
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Belen'kii L. I., Poddubny I. S., Krayushkin M. M. Reaction of Trichloromethylarenes with Pyridine: A Novel Synthesis of N-(4-Pyridyl)pyridinium Salts and Aromatic Aldehydes // Mendeleev Communications. 1993. Vol. 3. No. 3. pp. 97-98.
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TY - JOUR
DO - 10.1070/MC1993v003n03ABEH000240
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n03ABEH000240
TI - Reaction of Trichloromethylarenes with Pyridine: A Novel Synthesis of N-(4-Pyridyl)pyridinium Salts and Aromatic Aldehydes
T2 - Mendeleev Communications
AU - Belen'kii, Leonid Isaakovich
AU - Poddubny, Igor Sergeyevich
AU - Krayushkin, Mikhail Mikhailovich
PY - 1993
DA - 1993/06/30
PB - Mendeleev Communications
SP - 97-98
IS - 3
VL - 3
ER -
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@article{1993_Belen'kii,
author = {Leonid Isaakovich Belen'kii and Igor Sergeyevich Poddubny and Mikhail Mikhailovich Krayushkin},
title = {Reaction of Trichloromethylarenes with Pyridine: A Novel Synthesis of N-(4-Pyridyl)pyridinium Salts and Aromatic Aldehydes},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n03ABEH000240},
number = {3},
pages = {97--98},
doi = {10.1070/MC1993v003n03ABEH000240}
}
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Belen'kii, Leonid Isaakovich, et al. “Reaction of Trichloromethylarenes with Pyridine: A Novel Synthesis of N-(4-Pyridyl)pyridinium Salts and Aromatic Aldehydes.” Mendeleev Communications, vol. 3, no. 3, Jun. 1993, pp. 97-98. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n03ABEH000240.

Abstract

We have shown that in reductive condensation of trichloromethylarenes with hydroxylamine and hydrazines in pyridine the reduction stage, involving the exchange of one chlorine atom for a hydrogen atom, can proceed without participation of hydroxylamine or hydrazine via the interaction of trichloromethylarene with pyridine leading to the formation of N-[N′-(α-chlorobenzyl- 4-pyridyl)]pyridinium salts which give after hydrolysis N-(4-pyridyl)pyridinium dichloride and respective aromatic aldehydes in high yields.

References

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Izv. Akad. Nauk SSSR. Ser. Khim., 1989
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Effect of Surfaces on the McFadyen-Stevens Aldehyde Synthesis; An Improved Procedure
Newman M.S., Caflisch E.G.
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