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Homolytic and Conjugate Addition of Thiols to 2,4-Dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane

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Abstract

Homolytic reaction of 1-propane- and 1-pentanethiols to 2,4-dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane, initiated by di-tert-butyl peroxide at 130°C, yields a mixture of isomeric sulfides (95%) as a result of addition at the α- and β-positions of the vinyl group. Conjugate addition of alkanethiols in the presence of the corresponding sodium thiolate at 100°C gives 10% of the same α- and β-regioisomeric sulfides at a ratio of 1:20.

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Authors and Affiliations

  1. Ufa State Petroleum Technical University, ul. Kosmonavtov 1, Ufa, 450062, Bashkortostan, Russia

    R. M. Makaeva, V. V. Zorin, R. R. Musavirov, L. S. Brod'ko, S. V. Gvozdik & R. S. Musavirov

  2. Research Institute of Fine Chemicals, Ufa, Bashkortostan, Russia

    R. M. Makaeva, V. V. Zorin, R. R. Musavirov, L. S. Brod'ko, S. V. Gvozdik & R. S. Musavirov

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  1. R. M. Makaeva
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  2. V. V. Zorin
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  3. R. R. Musavirov
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  4. L. S. Brod'ko
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  5. S. V. Gvozdik
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  6. R. S. Musavirov
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Makaeva, R.M., Zorin, V.V., Musavirov, R.R. et al. Homolytic and Conjugate Addition of Thiols to 2,4-Dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane. Russian Journal of Organic Chemistry 37, 442–445 (2001). https://doi.org/10.1023/A:1012457213707

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