Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Thermolysis Reactions of 2-Methoxy-2-(o-N,N-dimethylminometiyl)-phenyl-3-tiimetiylsilyl-5,5-dimetiyl-2-silahexane

  • Published : 20000800
Download PDF
⟨ Previous Next ⟩

Abstract

In the neat flow vacuum pyrolysis of 2-methoxy-2-(o-N,N+dimethylaminomethyl)phenyl-3-trimethylsilyl-5,5-dime-thyl-2-silahexane (4) at $600^{\circ}C$ and its static thermolysis at $350^{\circ}C23-benzo-5-aza-1-silacyclohexane$, (5) has been obtained in97% and 46％ y ields, respectively. Product 5 might have been formed via an intramolecular rearrangement invoIving a zwitterionic species generated from the pentacoordinated silene Si-atom. From trapping experiments with an excess of MeOH, we have obtained 2-(o-N,N-dimethylaminomethyl)phenyl-5,5-dimethyl-2-trimethylsiloxy-2-silahexane (6) and 2-(o-N,N-dimethylaminomethyl)phenyl-2-methoxy-5,5-dime-thyl-2-silahexane (7) formed via an intermolecular protodesilylation reaction rather than through trapped prod-ucts of the silene.

Keywords

References

  1. Chem. Commun. Gusel'nikov, L. E.;Flowers, M. C.
  2. J. Organomet. Chem. v.201 Ishikawa, M.;Nakagawa, K. I.;Enokida, R.;Kumada, M.
  3. J. Organomet. Chem. v.184 Sakurai, H.;Nakadaira, Y.;Kira, M.;Sugiyama, H.;Yoshida, K.;Takiguchi, T.
  4. Organometallics v.8 Jung, I. N.;Pae, D. H.;Yoo, B. R.;Lee, M. E.;Jones, P. R.
  5. J. Am. Chem. Soc. v.96 Seyferth, D.;Lefferts, J. L.
  6. J. Organomet. Chem. v.273 Wiberg, N.
  7. Angew. Chem. Int. Ed. Engl. v.16 Wiberg, N.;Preiner, G.
  8. J. Chem. Soc.;Chem. Commun. Brook, A. G.;Abdesaken, F.;Gutekunst, B.;Gutekunst, G.;Kallury, R. K.
  9. J. Am. Chem. Soc. v.104 Brook, A. G.;Nyburg, S. C.;Abdesaken, F.;Gutekunst, G.;Kallury, R. K.;Poon, Y. C.;Chang, Y.;Wang-Ng, W.
  10. J. Organomet. Chem. v.315 Wiberg, N.;Kopf, H.
  11. J. Organomet. Chem. v.271 Wiberg, N.;Wagner, G.
  12. The Chemistry of Organic Silicon Compounds Apeloig, Y.;Patai, S.(ed.);Rappoport, Z.(ed.)
  13. The Chemistry of Organic Silicon Compounds Corriu, R. J. P.;Young, J. C.;Patai, S.(ed.);Rappoport, Z.(ed.)
  14. Organometallics v.14 Belzner, J.;Ihmels, H.;Kneisel, B. O.;Gould, R. O.;Herbst-Irmer, R.
  15. Organometallics v.14 Belzner, J.;Schar, D.;Ihmels, H.;Kneisel, B. O.;Herbst-Irmer, R.
  16. Naturforsch v.47b Auner, N.;Penzenstadler, E.;Herdtweck, E. Z.
  17. Adv. Organomet. Chem. v.39 Brook, A. G.;Brook, M. A.
  18. J. Am. Chem. Soc. v.105 Jones, P. R.;Lee, M. E.