Advertisement

1-Methyl-1-Vinyl-3,3,5,5-Tetraphenylcyclotrisiloxane: An Organofunctional Cyclotrisiloxane

  • Chip Nataro
  • William M. Cleaver
  • Christopher W. Allen
Communication

Abstract

The characterization of 1-methyl-1-vinyl-3,3,5,5-tetraphenylcyclotrisiloxane by NMR(1H,13C,29Si) and X-ray crystallography is reported. The central siloxane ring is planar with Si–O bond lengths and angles which are similar to those found in the structures of other cyclotrisiloxanes. There is significant thermal motion of the methyl and vinyl groups. Very low incorporation of the siloxane is observed in the radical catalyzed copolymerization of the siloxane with styrene.

Keywords

Cyclosiloxane Vinylsiloxane X-ray Addition polymerization 

Notes

Acknowledgment

The authors would like to thank Vermont EPSCoR for financial support of this project.

References

  1. 1.
    H.R. Allcock, Chemistry and Applications of Polyphosphazenes (Wiley-Interscience, Hoboken, New Jersey, 2003)Google Scholar
  2. 2.
    V. Chandrasekhar, Inorganic and Organometallic Polymers (Springer-Verlag, Heildelberg, 2005)Google Scholar
  3. 3.
    C.W. Allen, Trends Polym. Sci. 2, 342 (1994)Google Scholar
  4. 4.
    J.C. van de Grampel, in Synthesis and Characterization of Poly(organophosphazenes), Chapter 7, ed. by M. Gleria, R. DeJaeger (Nova Science Publishers, New York, 2004)Google Scholar
  5. 5.
    L. McNally, C.W. Allen, Heteroatom. Chem. 4, 159 (1993)CrossRefGoogle Scholar
  6. 6.
    J. Schwab, J. Lichtenhan, J. Appl. Organomet. Chem. 12, 707 (1998)CrossRefGoogle Scholar
  7. 7.
    A.A. Zhdanov, B.G. Zavin, O.G. Blokhina, Vysokomol. Soedin. Ser. B 25, 582 (1983)Google Scholar
  8. 8.
    K.A. Andrianov, O.G. Blokhina, B.G. Zavin, N.V. Pertsova, Vysokomol. Soedin. Ser. A 19, 434 (1997)Google Scholar
  9. 9.
    R.C. Sporck, U.S. Patent, US 3340287 (1967)Google Scholar
  10. 10.
    P.I. Prescott, T.G. Selin, U.S. Patent, US 3222369, 1965Google Scholar
  11. 11.
    C.N. Myer, C.W. Allen, J. Inorg. Organomet. Polym. Mater. 17, 143 (2007)CrossRefGoogle Scholar
  12. 12.
    XSCANS. X-ray Single Crystal Analysis System. Version 2.1., Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, 1994Google Scholar
  13. 13.
    G.M. Sheldrick, SHELXTL/PC User’s Manual. Siemens Analytical X-ray Instruments Inc (Madison, Wisconsin, 1990)Google Scholar
  14. 14.
    G.M. Sheldrick, SHELX193 Program for the Refinement of Crystals Structures (University of Göttingen, Germany, 1993)Google Scholar
  15. 15.
    U. Wannagat, G. Bogedian, A. Schervan, H.C. Marsmann, D.J. Brauer, H. Bürger, F. Dörrenbach, G. Pawelke, C. Krüger, K.-H. Claus, Z. Naturforsch 45b, 931 (1991)Google Scholar
  16. 16.
    R. Pomes-Hernandez, Y. Smolin, Y. Shepelev, Rev. Cubana Fis. 2, 153 (1982)Google Scholar
  17. 17.
    G. Pyronel, Atti Accad. Naz. Lincei 16, 231 (1954)Google Scholar
  18. 18.
    R.P. Hernandez, Acta Crystallogr. Sect. A: Cryst. Phys. Diffr. Theor. Crystallogr. 34, S406 (1978)CrossRefGoogle Scholar
  19. 19.
    W. Clegg, Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. 38, 1648 (1982)CrossRefGoogle Scholar
  20. 20.
    H.-W. Lerner, S. Scholz, N. Wiberg, K. Polborn, M. Bolte, M. Wagner, Z. Anorg. Allg. Chem. 631, 1863 (2005)CrossRefGoogle Scholar
  21. 21.
    Yu.E. Ovchinnikov, Yu.T. Struchkov, M.I. Buzin, V.S. Papkov, Vysokomol. Soedin Ser. B 39, 430 (1997)Google Scholar
  22. 22.
    B. Ziemer, M. Bacher, N. Auner, N. Act. Cryst. C54, 1111 (1998)CrossRefGoogle Scholar
  23. 23.
    P.E. Tomlins, J.E. Lydon, D. Akrigg, B. Sheldrick, Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 41, 292 (1985)CrossRefGoogle Scholar
  24. 24.
    J.F. Hyde, L.K. Frevel, H.S. Nutting, P.S. Petrie, M.A. Purcell, J. Am. Chem. Soc. 69, 488 (1947)CrossRefGoogle Scholar
  25. 25.
    N.G. Bokii, G.N. Zakharova, Y.T. Struchkov, Zh. Strukt. Khim 13, 291 (1972)Google Scholar
  26. 26.
    Y.E. Ovchinnikov, V.E. Shklover, Y.T. Struchkov, L.M. Tartakovskaya, N.G. Vasilenko, A.A. Zhdanov, Metalloorg. Khim 1, 1126 (1988)Google Scholar
  27. 27.
    A.A. Ahdab, G. Rima, H. Gornitzka, J. Barrau, J. Organomet. Chem. 658, 94 (2002)CrossRefGoogle Scholar
  28. 28.
    M.J. MacLachlan, J. Zheng, A.J. Lough, I. Manners, C. Mordas, R. LeSuer, W.E. Geiger, L.M. Liable-Sands, A.L. Rheingold, Organomet 18, 1337 (1999)CrossRefGoogle Scholar
  29. 29.
    O.I. Cherenkova, N.V. Alekseev, A.I. Gusev, J. Struct. Chem. 16, 504 (1975)Google Scholar
  30. 30.
    V.E. Shklover, N.G. Bokii, Y.T. Struchkov, K.A. Andianov, B.G. Zavin, V.S. Svistunov, J. Struct. Chem. 15, 841 (1974)CrossRefGoogle Scholar
  31. 31.
    D. Schmidt-Böse, U. Klingebiel, Chem. Ber. 123, 449 (1990)CrossRefGoogle Scholar
  32. 32.
    T. Buschen, W. Dietz, U. Klingebiel, M. Noltemeyer, Y. Schwerdtfeger, Z. Naturforsch. B: Chem. Sci. 62, 1358 (2007)Google Scholar
  33. 33.
    Y. Itami, B. Marciniec, M. Kubicki, Organometallics 22, 3717 (2003)CrossRefGoogle Scholar
  34. 34.
    R. Gewald, U. Scheim, K. Ruhlmann, H. Goesman, D. Fenske, J. Organomet. Chem. 450, 73 (1993)CrossRefGoogle Scholar
  35. 35.
    S.T. Malinovsky, A.T. Vallina, H. Stoeckli-Evans, Zh. Strukt. Khim 47, 1143 (2006)Google Scholar
  36. 36.
    M. Seno, M. Hasegawa, T. Hirano, T. Sato, J. Polym. Sci. A: Polym. Chem. 43, 5864 (2005)CrossRefGoogle Scholar
  37. 37.
    J.G. DuPont, C.W. Allen, Macromolecules 12, 169 (1979)CrossRefGoogle Scholar
  38. 38.
    C.W. Allen, R.P. Bright, Macromolecules 19, 571 (1986)CrossRefGoogle Scholar
  39. 39.
    M.A. Hempenius, R.G.H. Lammerink, G.J. Vansco, Macromolecules 30, 266 (1997)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • Chip Nataro
    • 1
    • 2
  • William M. Cleaver
    • 1
  • Christopher W. Allen
    • 1
  1. 1.Department of ChemistryUniversity of VermontBurlingtonUSA
  2. 2.Department of ChemistryLafayette CollegeEastonUSA

Personalised recommendations