Bulletin of the Korean Chemical Society

  • 제18권9호
  • /
  • Pages.998-1002
  • /
  • 1997
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

[4+4] Cyclodimer of tert-Butyl 9-Anthroate and Furan and [4+4] Cyclodimers of Alkyl 9-Anthroate

  • 발행 : 1997.09.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Irradiation of tert-butyl 9-anthroate and furan through a Uranium glass filter gave the [4+4] cyclodimer (21.8%) of tert-butyl 9-anthroate and furan and the 1,4-10',9' cyclodimer (4.2%) of tert-butyl 9-anthroate as well as the 9,10-10',9' cyclodimer (65.7%) of tert-butyl 9-anthroate. The [4+4] cyclodimer of tert-butyl 9-anthroate and furan was found to be thermally dissociated into their unit components with the activation enthalpy of 35.6 kcal/mole and the activation entropy of 7.6 eu, and photochemically dissociated to produce excited tert-butyl 9-anthroate. Quantum yields for the photodissociation to tert-butyl 9-anthroate and the formation of excited tert-butyl 9-anthroate in cyclohexane at room temperature were determined to be 0.56 and 0.19, respectively. The 1,4-10',9' cyclodimer of tert-butyl 9-anthroate in DMF was thermally dissociated into tert-butyl 9-anthroate with the activation enthalpy of 34.8 kcal/mole and the activation entropy of 16.4 eu. Upon irradiation, the [4+4] cyclodimers of tert-butyl 9-anthroate and the [4+4] cyclodimers of methyl 9-anthroate were quantitatively dissociated. However, no adiabatic photoreversion was observed from any of the cyclodimers. Quantum yields for the photodissociation in cyclohexane at room temperature were measured and compared.

키워드

참고문헌

  1. Chem. Rev. v.87 McCullough, J. J.
  2. J. Am. Chem. Soc. v.109 Yang, N. C.;Yang, X.
  3. Bull. Chem. Soc. Jpn. v.67 Kimura, M.;Okamoto, H.;Kashino, S.
  4. J. Am. Chem. Soc. v.104 Yang, N. C.;Chen, M.-J.;Chen. P.;Mak, K. T.
  5. J. Am. Chem. Soc. v.106 Yang, N. C.;Chen, M.-J.;Chen, P.
  6. J. Org. Chem. v.53 Kimura, M.;Okamoto, H.;Kura, H.;Okazaki, A.;Nagayasu, E.;Satake, K.;Morosawa, S.;Fukazawa, M.;Abdel-Halim, H.;Cowan, D. O.
  7. J. Chem. Soc., Perkin Trans. v.Ⅰ Kimura, M.;Kura, H.;Nukada, K.;Okamoto, H.;Satake, K.;Morosawa, S.Ⅰ
  8. Bull. Chem. Soc. Jpn. v.66 Okamoto, H.;Kimura, M.;Satake, K.;Morosawa, S.
  9. Tetrahedron Lett. v.52 Noh, T.;Kim, D.
  10. Bull. Korean Chem. Soc. v.18 Noh, T.;Kim, D.;Jang, S.
  11. J. Org. Chem. v.52 Albini, A.;Fasani, E.;Faiardi, D.
  12. J. Am. Chem. Soc. v.110 Albini, A.;Fasani, E.
  13. J. Am. Chem. Soc. v.110 Yang, N. C.;Noh, T.;Gan, H.;Halfon, S.;Hrnjez, B. J.
  14. Bull. Korean Chem. Soc. v.18 Noh, T.;Lim, H.;Kim, D.
  15. Chem. Lett. Noh, T.;Lim. H.
  16. J. Phys. Chem. v.79 Shon, R. S. -L.;Cowan, D. O.;Schmiegel, W. W.
  17. J. Phys. Chem. v.80 Werner, T. C.;Matthews, T.;Soller, B.
  18. Tetrahedron Lett. v.26 Felix, G.;Lapouyade, R.;Bouas-Laurent, H.;Clin, B.
  19. Chem. Phys. Lett. v.78 Ferguson, J.;Castellan, A.;Desvergne, J.-P.;Bouas-Laurent, H.
  20. J. Chem. Soc., Perkin Trans. Ⅱ Desvergne, J.-P.;Bitit, N.;Castellan, A.;Webb, M.;Bouas-Lauren, H.
  21. J. Chem. Soc. Chem. Commun. Fages, F.;Desvergne, J.-P.;Frisc, I.;Bouas-Laurent, H.;
  22. J. Photochem. Photobiol. A: Chem. v.97 Becker, H.-D.;Becker, H.-C.;Langer, V.
  23. Elements of Organic Photochemistry Cowan, D. O.;Drisko, R. L.
  24. Photochromism; Molecules and Systems Bouas-Laurent, H.;Desvergne, J.-P.;Durr, H.(Ed.);Bouas-Laurent, H.(Ed.)
  25. Helv. Chim. Acta. v.57 Belus, D.;Rist, G.
  26. J. Am. Chem. Soc. v.97 Kabakoff, D. S.;Bunzli, J.-C. G.;Oth, J. F. M.;Hammond, W. B.;Berson, J. A.
  27. Chem. Phys. Lett. v.88 Okada. T.;Kida, K.;Mataa, N.
  28. J. Am. Chem. Soc. v.105 Smothers, W. K.;Saltiel, J.
  29. Resonance in Organic chemistry Wheland, G. W.
  30. Angew. Chem. Int. Ed. Engl. v.18 Turro, N. J.;McVey, J.;Ramamurthy, V.;Lechtken, P.
  31. Photolumunescence of Solutions Parker, C. A.
  32. Handbook of Photochemistry Murov, S. L.