Preparation and Polymerization of Alkenylsilanes

Alkenylsilane의 제조와 고분자화반응

  • 김정균 (동아대학교 자연과학대학 화학과) ;
  • 최순규 (동아대학교 자연과학대학 화학과) ;
  • 박은미 (동아대학교 자연과학대학 화학과) ;
  • 정인경 (동아대학교 자연과학대학 화학과)
  • Published : 19970200

Abstract

The silyltriflates$(Ph_{3-n}SiH(OTf)_n)$have been produced by the reaction of triphenylsilane and triflic acid$(CF_3SO_3H)$at low temperature. These highly reactive compounds are a valuable reagent for the synthesis of numerous new functional substituted silane derivatives. The reaction of silyltriflates with alkenyl- and alkynylmagnesium bromide as well as organolithium compounds gave new silanes$Ph_2SiHR(R=\;C(CPh,\;CH=CH_2,\;CH_2CH=CH_2,\; (CH_2)_2CH=CH_2,\;(CH_2)_3CH=CH_2)$in high yields. The hydrosilation of prepared alkenyl- and alkynylsilanesPh_2SiHR$in the presence of a platinum catalyst(Pt/C) at high temperature$(200{\circ}C)$gave carbosilane polymers$((Ph_2SiCH=CPh)_n$and$(Ph_2Si(CH_2)m)n;\;m=2∼4, n{\ge}10)$along with five- and six-membered silaalkane ring compounds derived from intramolecular hydrosilation reactions. All of the prepared compounds are confirmed by NMR, UV, IR and mass spectroscopy as well as elemental analysis.

Keywords

References

  1. Frontiers of Organosilicon Chemistry Basindale, A. R.;Gasper, P. P.
  2. Proceedings of the VIIth International Symposium on Organosilicon Chemistry Ni, H.-Z.;Ishikawa, M.;Nate, K.;Matsuzaki, K.;Kumada, M.
  3. US-A 2563004 v.122 Clark, H. A.
  4. Advanced in Silicon Chemistry Larson, G. L.
  5. Organometallics v.8 Ishikawa, M.;Hasekawa, Y.;Kunai, A.;Yamanaka, T.
  6. Macromolecules v.23 Iwahara, T.;Hayase, S. H.;West, R.
  7. Organosilicon Chemisty Ⅱ Auner, N.;Weis, J.
  8. Organometallics v.8 Ischikawa, M.;Hasegawa, Y.;Kunai, A.;Yamanaka, T.
  9. J. Organomet. Chem. v.381 Ischikawa, M.;Hasegawa, Y.;Kunai, A.;Yamanaka, T.
  10. Macromolecules v.25 Ohshita, J.;Matsuguchi, A.;Furumori, K.;Hong, R.;Ischikawa, M.;Yamanaka, T.;Koike, T.;Shioyo, J.
  11. Adv. Organomet. Chem. v.17 Speier, J. L.
  12. Organometallics v.13 Uhlig, W.
  13. J. Organomet. Chem. v.421 Uhlig, W. J.
  14. J. Organomet. Chem. v.436 Uhlig, W.;Tretner, C.
  15. J. Organomet. Chem. v.402 Uhlig, W.
  16. Z. Anorg. Allg. Chem. v.618 Uhlig, W.
  17. Z. Anorg. Allg. Chem. v.603 Uhlig, W.
  18. Adv. in Organosilicon Chem. v.1 Corey, J. Y.
  19. Organometallics v.14 Corey, J. Y.;Kraichely, D. M.;Huhmann, J. L.;Braddock-Wilking, J.;Lindeberg, A.
  20. Organometallics v.13 Corey, J. Y.;Kraichely, D. M.;Huhmann, J. L.;Braddock-Wilking, J.
  21. Organometallics v.11 Ishikawa, A.;Hatano, T.;Hasegawa, Y.;Horio, T.;Kunai, A.;Miyai, Y.;Ishida, M.;Ttsukihara, T.;Yamanaka, T.;Kioke, T.;Shioya, J.
  22. Organometallics v.11 Ischikawa, M.;Hatano, T.;Hasegawa, Y.;Horio, T.;Kunai, A.;Miyai, Y.;Ishida, T.;Tsukihara, T.;Yamanaka, T.;Koike, T.;Shioya, J.
  23. J. Organomet. Chem. v.409 Uhlig, W.
  24. J. Organomet. Chem. v.340 Matyaszevski, K.;Chen. Y. L.
  25. Macromolecules v.24 Ohshita, J.;Kanaya, D;Ishikawa, M.;Kocke, T.;Yamanaka, T.
  26. J. Organomet. Chem. v.456 Corriu, R. J. P.;Douglas, W. E.;Yang, Z.
  27. J. Am. Chem. Soc. v.107 Gleier, R.;Schafer, W.;Sakurai, H.
  28. Organometallics v.8 Ohshita, J.;Furumori, K.;Ischikawa, M.;Yamanaka, T.
  29. J. Organomet. Chem. v.378 Uhlig, W.;Tzchach, A.
  30. Pure Appl. Chem. v.63 Ischikawa, M.
  31. Z. Anorg. Allg. Chem. v.601 Uhlig, W.
  32. Organicum Hazzard, B. Z.
  33. Chem. Ber. v.122 Hager, R.;Steigelmann, O.;Muller, G.;Schmidbauer, H.
  34. Organometallics v.6 Nate, U.;Ishikawa, M.;Ni, H.;Watanabe, H.;Saheki, Y.
  35. J. Korean Chem. Soc. v.38 Kim, C.;Park, E.;Son, B. Y.
  36. Organometallics v.10 Tanaka, K.;Nakajima, K.;Okada, M.;Yamabe, T.
  37. J. Chem. Soc., Chem. Commun. Iwahara, T.;West, R.
  38. J. Organomet. Chem. v.421 Uhlig. W.
  39. J. Korean Chem. Soc. v.40 Kim, C.;Park, E.;Jung, I.
  40. Chem. Ber. v.125 Uhlig. W.