Anti-Markovnikov addition of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole to trimethoxy(vinyl)silane under solvent- and catalyst-free conditions
O.M Trofimova
1
,
E. A. Grebneva
1
,
Yu I Bolgova
1
,
D. V. Pavlov
1
,
T I Vakulskaya
1
,
A I Emelyanov
1
,
Publication type: Journal Article
Publication date: 2020-06-01
scimago Q3
wos Q2
SJR: 0.385
CiteScore: 4.1
Impact factor: 2.4
ISSN: 0022328X, 18728561
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The addition of 2-mercaptobenzoxazole or 2-mercaptobenzothiazole to trimethoxy(vinyl)silane was studied. The thiol-ene reaction leads to previously unknown carbofunctional (trimethoxysilyl)ethyl derivatives of 2-mercaptobenzazoles C6H4N(Y)CS(CH2)2Si(OMe)3 (Y = O, S) with anti-Markovnikov orientation. The proposed mechanism is confirmed by EPR spectroscopy and quantum chemical calculations.
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Trofimova O. et al. Anti-Markovnikov addition of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole to trimethoxy(vinyl)silane under solvent- and catalyst-free conditions // Journal of Organometallic Chemistry. 2020. Vol. 917. p. 121269.
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Trofimova O., Grebneva E. A., Bolgova Yu. I., Pavlov D. V., Vakulskaya T. I., Emelyanov A. I., Pozdnyakov A. S. Anti-Markovnikov addition of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole to trimethoxy(vinyl)silane under solvent- and catalyst-free conditions // Journal of Organometallic Chemistry. 2020. Vol. 917. p. 121269.
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TY - JOUR
DO - 10.1016/j.jorganchem.2020.121269
UR - https://linkinghub.elsevier.com/retrieve/pii/S0022328X20301716
TI - Anti-Markovnikov addition of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole to trimethoxy(vinyl)silane under solvent- and catalyst-free conditions
T2 - Journal of Organometallic Chemistry
AU - Trofimova, O.M
AU - Grebneva, E. A.
AU - Bolgova, Yu I
AU - Pavlov, D. V.
AU - Vakulskaya, T I
AU - Emelyanov, A I
AU - Pozdnyakov, Alexander S.
PY - 2020
DA - 2020/06/01
PB - Elsevier
SP - 121269
VL - 917
SN - 0022-328X
SN - 1872-8561
ER -
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BibTex (up to 50 authors)
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@article{2020_Trofimova,
author = {O.M Trofimova and E. A. Grebneva and Yu I Bolgova and D. V. Pavlov and T I Vakulskaya and A I Emelyanov and Alexander S. Pozdnyakov},
title = {Anti-Markovnikov addition of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole to trimethoxy(vinyl)silane under solvent- and catalyst-free conditions},
journal = {Journal of Organometallic Chemistry},
year = {2020},
volume = {917},
publisher = {Elsevier},
month = {jun},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0022328X20301716},
pages = {121269},
doi = {10.1016/j.jorganchem.2020.121269}
}