Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane
V V Astakhova
1
,
Vera V Astakhova
2, 3, 4, 5
,
Mikhail Yu Moskalik
1
,
Bagrat A. Shainyan
1, 2, 3, 4, 5
3
Siberian branch of the Russian Academy of sciences
4
664033 Irkutsk
|
5
Russia
|
Publication type: Journal Article
Publication date: 2019-08-09
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
31418436
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The reaction of trimethyl(vinyl)silane with sulfonamides in the presence of N-bromosuccinimide was shown to proceed regioselectively in methylene chloride under mild conditions and led to the products of bromosulfamidation in up to 88% yield. The obtained adducts undergo base-promoted dehydrobromination to give 2-trimethylsilyl-N-sulfonyl aziridines in a close to quantitative yield. In the reaction with trifluoromethanesulfonamide in acetonitrile or tetrahydrofuran, the Ritter-type (solvent-interception) products were obtained and converted to 1-triflyl-2-methyl-5-(trimethylsilyl)-2-imidazoline or 4-triflyl-3-(trimethylsilyl)-1,4-oxazocane in almost quantitative yield.
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28
Total citations:
28
Citations from 2024:
6
(21.42%)
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GOST
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Astakhova V. V. et al. Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 34. pp. 7927-7937.
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Astakhova V. V., Astakhova V. V., Moskalik M. Yu., Shainyan B. A. Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 34. pp. 7927-7937.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/c9ob01689a
UR - https://xlink.rsc.org/?DOI=C9OB01689A
TI - Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane
T2 - Organic and Biomolecular Chemistry
AU - Astakhova, V V
AU - Astakhova, Vera V
AU - Moskalik, Mikhail Yu
AU - Shainyan, Bagrat A.
PY - 2019
DA - 2019/08/09
PB - Royal Society of Chemistry (RSC)
SP - 7927-7937
IS - 34
VL - 17
PMID - 31418436
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Astakhova,
author = {V V Astakhova and Vera V Astakhova and Mikhail Yu Moskalik and Bagrat A. Shainyan},
title = {Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane},
journal = {Organic and Biomolecular Chemistry},
year = {2019},
volume = {17},
publisher = {Royal Society of Chemistry (RSC)},
month = {aug},
url = {https://xlink.rsc.org/?DOI=C9OB01689A},
number = {34},
pages = {7927--7937},
doi = {10.1039/c9ob01689a}
}
Cite this
MLA
Copy
Astakhova, Vera V., et al. “Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane.” Organic and Biomolecular Chemistry, vol. 17, no. 34, Aug. 2019, pp. 7927-7937. https://xlink.rsc.org/?DOI=C9OB01689A.