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Photochemistry of Conjugated Poliynes : Photochemical Generation of Silacyclopropenes from 1-Aryl-4-(pentamethyldisilanyl)buta-1,3-diynes

  • Published : 1995.10.20

Abstract

No fluorescence was observed from 1-aryl-4-(pentamethyldisilanyl)buta-1,3-diynes except 1-(1-naphthyl)-4-(pentamethyldisilanyl)buta-1,3-diyne. Irradiation of 1-aryl-4-(pentamethyldisilanyl)buta-1,3-diynes (1) with methanol gives photoaddition products in relatively low yields compared to arylethynyldisilanes which show dual fluorescence. Irradiation of 1 with acetone yields site specific and regioselective 1:1 photoadducts through silacyclopropene intermediates. The triplet excited state of the silacyclopropene reacts with acetone to give addition photoproducts and the triplet energy of the silacyclopropenes lies around 260-286 kJ/mol.

Keywords

References

  1. J. Am. Chem. Soc. v.98 Conlin, R. T.;Gasper, P. P.
  2. J. Chem. Soc., Chem. Commun. v.352 Ishikawa, M.;Fuckikami, T.;Kumada, M.
  3. J. Organomet. Chem. v.194 Ishikawa, M.;Nishimura, K.;Sugisawa, H.;Kumada, M.
  4. J. Organomet. Chem. v.200 Sakurai, H.
  5. Tetrahedron Lett. v.34 Belzner, J.;Ihmels, H.
  6. Tetrahedron v.18 Vol'pin, M. E.;Koreshkov, Y. D.;Dulova, V. G.;Kursanov, D. N.
  7. J. Am. Chem. Soc. v.99 Ishikawa, M.;Fuchikami, Y.;Kumada, M.
  8. J. Am. Chem. Soc. v.99 Sakurai, H.;Kamiyama, Y.;Nakadaira, Y.
  9. J. Phys. Chem. v.91 Shizuka, H.;Okazaki, K.;Tanaka, H.;Tanaka, M.;Ishikawa, M.;Sumitani, M.;Yoshihara, K.
  10. J. Am. Chem. Soc. v.104 Ishikawa, M.;Sugisawa, H.;Fuchikami, Y.;Kumada, M.;Yamabe, T.;Kawakami, H.;Fukui, K.;Ueki, Y.;Shizuka, H.
  11. Organometallics v.31 Seyferth, D.;Vick, S. C.;Shannon, M. L.
  12. J. Organomet. Chem. v.272 Seyferth, D.;Annarelli, D. C.;Vick, S. C.
  13. J. Am. Chem. Soc. v.98 Seyferth, D.;Annarelli, D. C.;Vick, S. C.
  14. J. Org. Chem. v.59 Kwon, J. H.;Lee, S. T.;Hoshino, M.;Shim. S. C.
  15. J. Chem. Soc., Perkin Trans. v.2 Lee, S. T.;Shim, S. C.
  16. Purification of Laboratory Chemicals Perrin, D. D.;Armarego, W. L. F.
  17. J. Photochem. Photobiol. A: Chem. v.70 Lee, B. H.;Kim, M. S.;Shim, S. C.
  18. Photochem. Photobiol. v.54 Kim, M. S.;Lee, K. T.;Lee, B. H.;Shim, S. C.
  19. Handbook of Photochemistry;Marcel Dekker, Murov, S. L.