Anti-Markovnikov addition of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole to trimethoxy(vinyl)silane under solvent- and catalyst-free conditions

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...

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Bibliographic Details
Published in:Journal of organometallic chemistry 2020-06, Vol.917, p.121269, Article 121269
Main Authors: Trofimova, O.M., Grebneva, E.A., Bolgova, Yu.I., Pavlov, D.V., Vakul’skaya, T.I., Emel’yanov, A.I., Pozdnyakov, A.S.
Format: Article
Language:English
Subjects:
2-Mercaptobenzothiazole
2-Mercaptobenzoxazole
DFT calculations
EPR spectroscopy
Thiol-ene reaction
trimethoxy(vinyl)silane
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Summary: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. [Display omitted] •The addition of 2-mercaptobenzazole to trimethoxy(vinyl)silane was studied.•New (trimethoxysilyl)ethyl derivatives of 2-mercaptobenzazoles were obtained.•The thiol-ene reaction leads to unknown silanes with anti-Markovnikov orientation.•The mechanism of reaction is confirmed by EPR and quantum chemical calculations.
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2020.121269