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Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane

Anatoly Timofeevich Soldatenkov 1
Anatoly Timofeevich Soldatenkov
, 
Valerii Vladimirovich Shereshovets 1
Valerii Vladimirovich Shereshovets
, 
Lyudmila Nikolaevna Kuleshova 2
Lyudmila Nikolaevna Kuleshova
, 
10.1070/MC1998v008n05ABEH001011
Published 1998-09-10
Communication , Volume 8, Issue 5, 193-195
4
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Soldatenkov A. T. et al. Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane // Mendeleev Communications. 1998. Vol. 8. No. 5. pp. 193-195.
GOST all authors (up to 50) Copy
Soldatenkov A. T., Shereshovets V. V., Kuleshova L. N., Khrustalev V. N. Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane // Mendeleev Communications. 1998. Vol. 8. No. 5. pp. 193-195.
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TY - JOUR
DO - 10.1070/MC1998v008n05ABEH001011
UR - https://mendcomm.colab.ws/publications/10.1070/MC1998v008n05ABEH001011
TI - Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane
T2 - Mendeleev Communications
AU - Soldatenkov, Anatoly Timofeevich
AU - Shereshovets, Valerii Vladimirovich
AU - Kuleshova, Lyudmila Nikolaevna
AU - Khrustalev, Victor Nikolaevich
PY - 1998
DA - 1998/09/10
PB - Mendeleev Communications
SP - 193-195
IS - 5
VL - 8
ER -
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@article{1998_Soldatenkov,
author = {Anatoly Timofeevich Soldatenkov and Valerii Vladimirovich Shereshovets and Lyudmila Nikolaevna Kuleshova and Victor Nikolaevich Khrustalev},
title = {Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane},
journal = {Mendeleev Communications},
year = {1998},
volume = {8},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1998v008n05ABEH001011},
number = {5},
pages = {193--195},
doi = {10.1070/MC1998v008n05ABEH001011}
}
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Soldatenkov, Anatoly Timofeevich, et al. “Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane.” Mendeleev Communications, vol. 8, no. 5, Sep. 1998, pp. 193-195. https://mendcomm.colab.ws/publications/10.1070/MC1998v008n05ABEH001011.

Abstract

Potassium permanganate oxidizes a mixture of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (THP) 1 and dicyanomethane to 2-dicyanomethylidenetetrahydropyridine 2, but using manganese dioxide leads to the unusual oxidative hydroxymethylation of 1; subsequent treatment of the 3-hydroxymethyltetrahydropyridine 4 formed with aqueous potassium permanganate results in lactamination, accompanied by aromatization or oxodihydroxylation.

References

1.
10.1070/MC1998v008n05ABEH001011_bib1
Soldatenkov
Khim. Geterotsikl. Soedin., 1997
2.
10.1070/MC1998v008n05ABEH001011_bib2
Soldatenkov
Izv. Akad. Nauk, Ser. Khim., 1997
3.
Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis.
Langston J.W., Ballard P., Tetrud J.W., Irwin I.
Science, 1983
5.
10.1070/MC1998v008n05ABEH001011_bib5
Stewart
Oxidation in Organic Chemistry, 1965
6.
10.1070/MC1998v008n05ABEH001011_bib6
Soldatenkov
Khim. Geterotsikl. Soedin., 1996
7.
10.1070/MC1998v008n05ABEH001011_bib7
Saika
Book of Abstracts of the 12th International Conference on Organic Synthesis, 1998
8.
Soldatenkov A.T., Temesgen A.W., Bekro I.A., Khristoforova T.P., Soldatova S.A., Anissimov B.N.
Mendeleev Communications, 1997
9.
10.1070/MC1998v008n05ABEH001011_bib9
Chichibabin
Zhurnal Russkogo Fiziko-Khim Obshchestva, 1930