Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles
Publication type: Journal Article
Publication date: 2009-10-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
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.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Russian Journal of Physical Chemistry B
2 publications, 33.33%
|
|
|
Russian Journal of Organic Chemistry
1 publication, 16.67%
|
|
|
MolBank
1 publication, 16.67%
|
|
|
Heterocycles
1 publication, 16.67%
|
|
|
Advances in Heterocyclic Chemistry
1 publication, 16.67%
|
|
|
1
2
|
Publishers
|
1
2
3
|
|
|
Pleiades Publishing
3 publications, 50%
|
|
|
MDPI
1 publication, 16.67%
|
|
|
The Japan Institute of Heterocyclic Chemistry
1 publication, 16.67%
|
|
|
Elsevier
1 publication, 16.67%
|
|
|
1
2
3
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
6
Total citations:
6
Citations from 2024:
0
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Ostrovskii V. A. et al. Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles // Russian Chemical Bulletin. 2009. Vol. 58. No. 10. pp. 2147-2153.
GOST all authors (up to 50)
Copy
Ostrovskii V. A., Podkameneva M. E., Poplavskii V. S., Trifonov R. E. Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles // Russian Chemical Bulletin. 2009. Vol. 58. No. 10. pp. 2147-2153.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1007/s11172-009-0293-y
UR - https://doi.org/10.1007/s11172-009-0293-y
TI - Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles
T2 - Russian Chemical Bulletin
AU - Ostrovskii, V A
AU - Podkameneva, M E
AU - Poplavskii, V S
AU - Trifonov, R E
PY - 2009
DA - 2009/10/01
PB - Springer Nature
SP - 2147-2153
IS - 10
VL - 58
SN - 1066-5285
SN - 1573-9171
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2009_Ostrovskii,
author = {V A Ostrovskii and M E Podkameneva and V S Poplavskii and R E Trifonov},
title = {Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles},
journal = {Russian Chemical Bulletin},
year = {2009},
volume = {58},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1007/s11172-009-0293-y},
number = {10},
pages = {2147--2153},
doi = {10.1007/s11172-009-0293-y}
}
Cite this
MLA
Copy
Ostrovskii, V. A., et al. “Kinetics and mechanism of formation of isomeric 1-methyl- and 2-methyl-5-vinyltetrazoles.” Russian Chemical Bulletin, vol. 58, no. 10, Oct. 2009, pp. 2147-2153. https://doi.org/10.1007/s11172-009-0293-y.