Electrocycloreversion of benzocyclobutenols promoted by photoinduced electron transfer

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5547-5550

  Takahashi, Yasutake ^a   Miyamoto, Kazuya ^a   Sakai, Kazuhiro ^a   Ikeda, Hiroshi ^a   Miyashi, Tsutomu ^a   Ito, Yoshikatsu ^b   Tabohashi, Ken ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0030605822     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01152-5     Document Type: Article

References (30)

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21. 3) 19.84, 21.27, 37.35, 113.72 (CN), 114.25 (CN), 114.48 (CN), 114.65, 117.44, 119.24, 129.11, 129.20, 129.57, 131.18, 132.63, 134.44, 135.89, 135.93, 136.59, 136.96, 137.20, 140.22, 150.64, 199.79 (CO).
22. 9 Calculations by using Weller's equation suggest that free energy changes for electron-transfer quenching of the singlet excited TeCA by 1 are exothermic by -0.41, -0.70, and -0.65 eV for 1a, 1b, and 1c, respectively. Their oxidation potentials are +2.09, +1.80, and +1.85 V (vs. SCE), respectively.
23. 10 Sammes, P. G. Tetrahedron 1976, 32, 405-422. Ito, Y.; Nishimura, H.; Umehara, Y.; Yamada, Y.; Tone, M.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 1590-1597. Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965-6970. Wagner, P. J.; Subrahmanyam, D.; Park, B.-S. J. Am. Chem. Soc. 1991, 113, 709-710. See also references cited therein.
24. 10 Sammes, P. G. Tetrahedron 1976, 32, 405-422. Ito, Y.; Nishimura, H.; Umehara, Y.; Yamada, Y.; Tone, M.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 1590-1597. Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965-6970. Wagner, P. J.; Subrahmanyam, D.; Park, B.-S. J. Am. Chem. Soc. 1991, 113, 709-710. See also references cited therein.
25. 10 Sammes, P. G. Tetrahedron 1976, 32, 405-422. Ito, Y.; Nishimura, H.; Umehara, Y.; Yamada, Y.; Tone, M.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 1590-1597. Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965-6970. Wagner, P. J.; Subrahmanyam, D.; Park, B.-S. J. Am. Chem. Soc. 1991, 113, 709-710. See also references cited therein.
26. 10 Sammes, P. G. Tetrahedron 1976, 32, 405-422. Ito, Y.; Nishimura, H.; Umehara, Y.; Yamada, Y.; Tone, M.; Matsuura, T. J. Am. Chem. Soc. 1983, 105, 1590-1597. Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965-6970. Wagner, P. J.; Subrahmanyam, D.; Park, B.-S. J. Am. Chem. Soc. 1991, 113, 709-710. See also references cited therein.
27. 11 Nerdel, F.; Brodowski, W. Chem. Ber. 1968, 101, 1398-1406.
28. -1 was also obtained for the initial fast decay due to Z-4a.
29. 13 Uji-ie, K.; Kikuchi, K.; Kokubun, H. Chem. Lett. 1977, 499-502. Uji-ie, K.; Kikuchi, K.; Kokubun, H. J. Photochem. 1979, 10, 145-157.
30. 13 Uji-ie, K.; Kikuchi, K.; Kokubun, H. Chem. Lett. 1977, 499-502. Uji-ie, K.; Kikuchi, K.; Kokubun, H. J. Photochem. 1979, 10, 145-157.