DOI QR코드

DOI QR Code

An Estimation of the $\pi$-Bond Energy of 1-Methyl-1-Phenyl-2-Neopentylsilene

  • Lee Myong Euy (Department of Chemistry, Yonsei University) ;
  • Paul R. Jones (Department of Chemistry, University of North Texas)
  • 발행 : 1994.06.20

초록

The E-and Z-isomers of 1-methyl-l-phenyl-2-neopentylsilene, generated by the sealed tube thermolyses of their anthracene adducts are stereospecifically trapped by trimethylmethoxysilane to give diastereomeric adducts. The temperature dependence of the ratio of the two diastereomers obtained when the silene formed from the pure E-or Z-anthracene adduct was trapped at higher temperatures permitted the determination of an activation energy for the silene isomerization. The activation energies for the E-to Z-and Z-to E-silene isomerization are $45{\pm}$6 and $20{\pm}4$ kcal $mol^{-1}$, respectively. The significance of these values is discussed.

키워드

참고문헌

  1. The Chemistry of Organic Silicon Compounds Patai, S.;Rappoport, Z.
  2. Bull. Korean Chem. Soc. v.8 Lee, M. E.;Lee, J. K;Kim, C. H.
  3. Organometallics v.4 Cheng, A. H-B.;Jones, P. R.;Lee, M. E.;Roussi, P.
  4. J. Am. Chem. Soc. v.101 Brook, A. G.;Harris, J. W.;Lennon, J.;Sheikh, M. E.
  5. J. Am. Chem. Soc. v.104 Brook, A. G.;Nyburg, S. C.;Abdesaken, F.;Gutekunst, B.;Gutekunst, G.;Kallury, R. K. M. R.;Poon, Y. C.;Chang, Y.;Wong-Ng, W.
  6. Angew. Chem., Int. Ed. Engl. v.24 Wiberg, N.;Wagner, G.;Muller, G.
  7. Chem. Ber. v.119 Wiberg, N.;Wagner, G.
  8. J. Organomet. Chem. v.273 Wiberg, N.
  9. J. Am. Chem. Soc. v.105 Jones, P. R.;Lee, M. E.
  10. Silicon, Germanium, Tin and Lead Compounds v.9 no.1 Lee, M. E.;Jones, P. R.
  11. Organometallics v.2 Jones, P. R.;Lee, M. E.;Lin, L. T.
  12. J. Chem. Commun. v.104 Davidson, I. M. T.;Wood, I. T.
  13. Mechanism and Theory in Organic Chemistry Lowry, T. H.;Richardson, K. S.
  14. J. Chem. Phys. v.23 Douglas,J. E.;Rabinovitch, B. S.;Looney, F. S.
  15. Top. Sterochem. v.7 Kalinowski, H. O.;Kessler, H.
  16. Angew. Chem. Internat. Edit. v.9 Kessler, H.
  17. Ace. Chem. Res. v.14 Walsh, R.
  18. J. Phys. Chem. v.90 Walsh, R.
  19. Ber. Bunsenges Phys. Chem. v.86 Davidson, I. M. T.;Potzinger, P.;Riemann, B.
  20. J. Am. Chem. Soc. v.107 Schmidt, M. S.;GordonM. S.;Dupuis, M.

피인용 문헌

  1. Mechanism of the Thermal Z⇌E Isomerization of a Stable Silene; Experiment and Theory vol.131, pp.41, 2019, https://doi.org/10.1002/ange.201907864
  2. Mechanism of the Thermal Z⇌E Isomerization of a Stable Silene; Experiment and Theory vol.58, pp.41, 1994, https://doi.org/10.1002/anie.201907864