Kinetics and mechanism of 5-vinyltetrazole alkylation
Publication type: Journal Article
Publication date: 2008-11-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Alkylation of NH-unsubstituted 5-vinyltetrazole with methyl iodide in the presence of triethylamine in acetonitrile solution led to the formation of isomeric 1- and 2-methyl-5-vinyltetrazoles in 1:1 ratio. The reaction rate constants were measured at 25–55°C. According to the thermodynamic parameters of the reaction [ΔH ≠ 66 kJ mol−1, ΔS≠-74 (mol K)−1, 298 K] the limiting stage of the reaction consists in the electrophilic attack of methyl iodide on an H-complex of the heterocycle with triethylamine.
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Pavlyukova Yu. N. et al. Kinetics and mechanism of 5-vinyltetrazole alkylation // Russian Journal of Organic Chemistry. 2008. Vol. 44. No. 11. pp. 1711-1715.
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Pavlyukova Yu. N., Trifonov R. E., Yugai E. V., Aleshunin P. A., Tselinskii I. V., Ostrovskii V. A. Kinetics and mechanism of 5-vinyltetrazole alkylation // Russian Journal of Organic Chemistry. 2008. Vol. 44. No. 11. pp. 1711-1715.
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TY - JOUR
DO - 10.1134/s1070428008110249
UR - https://doi.org/10.1134/s1070428008110249
TI - Kinetics and mechanism of 5-vinyltetrazole alkylation
T2 - Russian Journal of Organic Chemistry
AU - Pavlyukova, Yu N
AU - Trifonov, R E
AU - Yugai, E V
AU - Aleshunin, P A
AU - Tselinskii, I V
AU - Ostrovskii, V A
PY - 2008
DA - 2008/11/01
PB - Pleiades Publishing
SP - 1711-1715
IS - 11
VL - 44
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2008_Pavlyukova,
author = {Yu N Pavlyukova and R E Trifonov and E V Yugai and P A Aleshunin and I V Tselinskii and V A Ostrovskii},
title = {Kinetics and mechanism of 5-vinyltetrazole alkylation},
journal = {Russian Journal of Organic Chemistry},
year = {2008},
volume = {44},
publisher = {Pleiades Publishing},
month = {nov},
url = {https://doi.org/10.1134/s1070428008110249},
number = {11},
pages = {1711--1715},
doi = {10.1134/s1070428008110249}
}
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MLA
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Pavlyukova, Yu. N., et al. “Kinetics and mechanism of 5-vinyltetrazole alkylation.” Russian Journal of Organic Chemistry, vol. 44, no. 11, Nov. 2008, pp. 1711-1715. https://doi.org/10.1134/s1070428008110249.