Hydrolilylation of 1-alkenes with dichlorosilane

Gerardus J.J. Out, G.J.J. Out, H.A. Klok, Leonore Schwegler, Holger Frey, H.H. Frey, M. Moller, Martin Möller

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Abstract

Symmetrically and unsymmetrically substituted diorganodichlorosilanes have been prepared by hydrosilylation with dichlorosilane using two different platinum catalysts, i.e., hexachloroplatinic acid (Speier's catalyst) and a platinum cyclovinylmethylsiloxane complex. Hydrosilylation of unsubstituted 1-alkenes proved to be very efficient, yielding anti-Markonikov substituted di-n-alkyldichlorosilanes. However, no reaction was observed when electron-deficient 1-alkenes were used. Octacarbonyldicobalt enabled formation of the monoadduct of 1H,1H,2H-perfluoro-1-hexene with dichlorosilane, which was employed in a second hydrosilylation of the olefin. Thus, the anti-Markovnikov diadduct was obtained in 40% overall yield. The two-step synthesis has also been applied successfully to obtain unsymmetrically substituted diorganodichlorosilanes containing nitrile and ether groups.
Original languageUndefined
Pages (from-to)185-194
JournalMacromolecular chemistry and physics
Volume196
Issue number196
DOIs
Publication statusPublished - 1995

Keywords

  • METIS-106130
  • IR-71211

Cite this

Out, G. J. J., Out, G. J. J., Klok, H. A., Schwegler, L., Frey, H., Frey, H. H., ... Möller, M. (1995). Hydrolilylation of 1-alkenes with dichlorosilane. Macromolecular chemistry and physics, 196(196), 185-194. https://doi.org/10.1002/macp.1995.021960112
Out, Gerardus J.J. ; Out, G.J.J. ; Klok, H.A. ; Schwegler, Leonore ; Frey, Holger ; Frey, H.H. ; Moller, M. ; Möller, Martin. / Hydrolilylation of 1-alkenes with dichlorosilane. In: Macromolecular chemistry and physics. 1995 ; Vol. 196, No. 196. pp. 185-194.
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title = "Hydrolilylation of 1-alkenes with dichlorosilane",
abstract = "Symmetrically and unsymmetrically substituted diorganodichlorosilanes have been prepared by hydrosilylation with dichlorosilane using two different platinum catalysts, i.e., hexachloroplatinic acid (Speier's catalyst) and a platinum cyclovinylmethylsiloxane complex. Hydrosilylation of unsubstituted 1-alkenes proved to be very efficient, yielding anti-Markonikov substituted di-n-alkyldichlorosilanes. However, no reaction was observed when electron-deficient 1-alkenes were used. Octacarbonyldicobalt enabled formation of the monoadduct of 1H,1H,2H-perfluoro-1-hexene with dichlorosilane, which was employed in a second hydrosilylation of the olefin. Thus, the anti-Markovnikov diadduct was obtained in 40{\%} overall yield. The two-step synthesis has also been applied successfully to obtain unsymmetrically substituted diorganodichlorosilanes containing nitrile and ether groups.",
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author = "Out, {Gerardus J.J.} and G.J.J. Out and H.A. Klok and Leonore Schwegler and Holger Frey and H.H. Frey and M. Moller and Martin M{\"o}ller",
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doi = "10.1002/macp.1995.021960112",
language = "Undefined",
volume = "196",
pages = "185--194",
journal = "Macromolecular chemistry and physics",
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Out, GJJ, Out, GJJ, Klok, HA, Schwegler, L, Frey, H, Frey, HH, Moller, M & Möller, M 1995, 'Hydrolilylation of 1-alkenes with dichlorosilane', Macromolecular chemistry and physics, vol. 196, no. 196, pp. 185-194. https://doi.org/10.1002/macp.1995.021960112

Hydrolilylation of 1-alkenes with dichlorosilane. / Out, Gerardus J.J.; Out, G.J.J.; Klok, H.A.; Schwegler, Leonore; Frey, Holger; Frey, H.H.; Moller, M.; Möller, Martin.

In: Macromolecular chemistry and physics, Vol. 196, No. 196, 1995, p. 185-194.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Hydrolilylation of 1-alkenes with dichlorosilane

AU - Out, Gerardus J.J.

AU - Out, G.J.J.

AU - Klok, H.A.

AU - Schwegler, Leonore

AU - Frey, Holger

AU - Frey, H.H.

AU - Moller, M.

AU - Möller, Martin

PY - 1995

Y1 - 1995

N2 - Symmetrically and unsymmetrically substituted diorganodichlorosilanes have been prepared by hydrosilylation with dichlorosilane using two different platinum catalysts, i.e., hexachloroplatinic acid (Speier's catalyst) and a platinum cyclovinylmethylsiloxane complex. Hydrosilylation of unsubstituted 1-alkenes proved to be very efficient, yielding anti-Markonikov substituted di-n-alkyldichlorosilanes. However, no reaction was observed when electron-deficient 1-alkenes were used. Octacarbonyldicobalt enabled formation of the monoadduct of 1H,1H,2H-perfluoro-1-hexene with dichlorosilane, which was employed in a second hydrosilylation of the olefin. Thus, the anti-Markovnikov diadduct was obtained in 40% overall yield. The two-step synthesis has also been applied successfully to obtain unsymmetrically substituted diorganodichlorosilanes containing nitrile and ether groups.

AB - Symmetrically and unsymmetrically substituted diorganodichlorosilanes have been prepared by hydrosilylation with dichlorosilane using two different platinum catalysts, i.e., hexachloroplatinic acid (Speier's catalyst) and a platinum cyclovinylmethylsiloxane complex. Hydrosilylation of unsubstituted 1-alkenes proved to be very efficient, yielding anti-Markonikov substituted di-n-alkyldichlorosilanes. However, no reaction was observed when electron-deficient 1-alkenes were used. Octacarbonyldicobalt enabled formation of the monoadduct of 1H,1H,2H-perfluoro-1-hexene with dichlorosilane, which was employed in a second hydrosilylation of the olefin. Thus, the anti-Markovnikov diadduct was obtained in 40% overall yield. The two-step synthesis has also been applied successfully to obtain unsymmetrically substituted diorganodichlorosilanes containing nitrile and ether groups.

KW - METIS-106130

KW - IR-71211

U2 - 10.1002/macp.1995.021960112

DO - 10.1002/macp.1995.021960112

M3 - Article

VL - 196

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EP - 194

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JF - Macromolecular chemistry and physics

SN - 1022-1352

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Out GJJ, Out GJJ, Klok HA, Schwegler L, Frey H, Frey HH et al. Hydrolilylation of 1-alkenes with dichlorosilane. Macromolecular chemistry and physics. 1995;196(196):185-194. https://doi.org/10.1002/macp.1995.021960112