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Addition of arylfluorosilanes containing silicon-attached hydrogen

Summary

  1. 1.

    In additions to unsaturated compounds in presence of a H2PtCl6 catalyst, hydride arylfluorosilanes are considerably more reactive than their chloro analogs.

  2. 2.

    The arylfluorosilyl groups of difluorophenylsilane and difluoro-1-naphthylsilane add at both of the carbon atoms of the vinyl group of styrene (mainly at the α-carbon atom), whereas the dichlorophenylsilyl group of dichlorophenylsilane adds only, to the end carbon atom of the double bond. The fluorodiphenylsilyl group of fluorodiphenylsilane adds to almost equal extents at both carbon atoms of the vinyl group of styrene.

  3. 3.

    In high-temperature condensation with chlorobenzene the replacement of the chlorine atoms of dichlorophenylsilane by fluorine atoms leads to a reduction in the ratio of condensation and reduction products.

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Literature cited

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    A. D. Petrov, V. F. Mironov, V. A. Ponomarenko, and E. A. Chernyshev, Synthesis of Organosilicon Monomers [in Russian] (Izd. AN SSSR, Moscow, 1961).

  2. 2.

    E. A. Chernyshev, M. E. Dolgaya, and A. D. Petrov, Izv. AN SSSR, Otd. khim. n.,1961, 1718.

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    L. Spialter, Tetrahedron Letters,1960, No. 5, 11.

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 650–654, April, 1965

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Chernyshev, E.A., Dolgaya, M.E. & Lubuzh, E.D. Addition of arylfluorosilanes containing silicon-attached hydrogen. Russ Chem Bull 14, 629–632 (1965). https://doi.org/10.1007/BF00846717

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Keywords

  • Chlorine
  • Carbon Atom
  • Double Bond
  • Hydride
  • Styrene