Mechanism of the cyclization of dimethyl diethynyl silane with selenium tetrabromide: Computational and structural studies, and monitoring

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Abstract

The structure of 2,4-dibromo-2-dibromomethyl-3,3-dimethyl-1-selena-3-silacyclopentene-4, formed by regioselective electrophilic addition of SeBr4to dimethyl diethynyl silane, has been determined using X-ray analysis technique. Quantum chemistry methods were used to study elementary stages of the reaction. It was found that the first stage consisted of SeBr4conversion into bimolecular complex Br2⋯SeBr2, initiated by dimethyl diethynyl silane. Possible formation of five-membered and six-membered heterocycles involves different cyclization mechanisms. The formation of only five-membered heterocycle is explained by kinetically preferable ring closure through four-center transition state. The conclusions obtained by calculations were confirmed by monitoring of the reaction using1H NMR method. © 2007 Elsevier B.V. All rights reserved.

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Amosova, S. V., Shagun, V. A., Martynov, A. V., Makhaeva, N. A., Larina, L. I., Lysenko, K. A., & Voronkov, M. G. (2007). Mechanism of the cyclization of dimethyl diethynyl silane with selenium tetrabromide: Computational and structural studies, and monitoring. Journal of Organometallic Chemistry, 692(16), 3307–3315. https://doi.org/10.1016/j.jorganchem.2007.01.023

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