Kinetics and mechanism of 5-vinyltetrazole alkylation

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 parameter...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2008-11, Vol.44 (11), p.1711-1715
Main Authors: Pavlyukova, Yu. N., Trifonov, R. E., Yugai, E. V., Aleshunin, P. A., Tselinskii, I. V., Ostrovskii, V. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary: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 [Δ H ≠ 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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428008110249