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

• Published in: Journal of organometallic chemistry Vol. 917; pp. 121269 - 121274
• 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: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 21.06.2020; Elsevier
• Subjects: 2-Mercaptobenzothiazole; 2-Mercaptobenzoxazole; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; DFT calculations; EPR spectroscopy; Physical Sciences; Science & Technology; Thiol-ene reaction; trimethoxy(vinyl)silane; 2-Mercaptobenzothiazole; 2-Mercaptobenzoxazole; Thiol-ene reaction; EPR spectroscopy; DFT calculations; trimethoxy(vinyl)silane; PHOTOCHEMICAL ADDITION; THIOLS; POLYMER; CHEMISTRY; THIYL RADICALS; DERIVATIVES; PBN
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2020.121269

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.