Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2009-10

AUTHORS

V. A. Ostrovskii, M. E. Podkameneva, V. S. Poplavskii, R. E. Trifonov

ABSTRACT

The alkylation of 5-(β-dimethylaminoethyl)tetrazole (1) with dimethyl sulfate afforded 5-(β-dimethylaminoethyl)-1-methyltetrazole (2) and 5-(β-dimethylaminoethyl)-2-methyltetrazole (3). The exhaustive alkylation of compounds 2 and 3 at the terminal dimethylamino group gave 1-methyl-(4) and 2-methyl-5-(β-trimethylammonioethyl)tetrazole (5) methyl sulfates. The proton elimination from the α-methylene (with respect to the tetrazole cycle) groups of the quaternary ammonium cations of salts 4 and 5 by the action of a base leads to the corresponding zwitterions 4± and 5±, which in the rate-determining step undergo the cleavage of the nitrogen—carbon bond with the formation of 1-methyl-5-vinyl- (6) and 2-methyl-5-vinyltetrazole (7). The true constant of the transformation of zwitterion 4± into tetrazole 6 is 21 times higher than that for the transformation of zwitterion 5± into tetrazole 7. More... »

PAGES

2147-2153

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-009-0293-y

DOI

http://dx.doi.org/10.1007/s11172-009-0293-y

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1023538242


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