Photoinduced heterolysis of the carbon-oxygen bond in bichromophoric 1- arylmethyloxy-2-pyridones

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9747-9750

  Sakurai, Tadamitsu ^a   Kubo, Kanji ^a,b   Kojima, Shunsuke ^a   Shoro, Takuya ^a   Inoue, Hiroyasu ^a  

^a KANAGAWA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDONE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; DRUG SYNTHESIS; IRRADIATION; LIGHT; LIGHT ABSORPTION; ULTRAVIOLET RADIATION;

EID: 0032564611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02282-5     Document Type: Article

References (20)

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4. 4. MacDonald, S. A.; Willson, C. G.; Fréchet, J. M. J. Acc. Chem. Res. 1994, 27, 151-158; Pirrung, M. C.; Huang, C.-Y. Tetrahedron Lett. 1995, 36, 5883-5884; Cameron, J. F.; Willson, C. G.; Fréchet, J. M. J. J. Am. Chem. Soc. 1996, 118, 12925-12937.
5. 4. MacDonald, S. A.; Willson, C. G.; Fréchet, J. M. J. Acc. Chem. Res. 1994, 27, 151-158; Pirrung, M. C.; Huang, C.-Y. Tetrahedron Lett. 1995, 36, 5883-5884; Cameron, J. F.; Willson, C. G.; Fréchet, J. M. J. J. Am. Chem. Soc. 1996, 118, 12925-12937.
6. 5. Pincock, J. A. Acc. Chem. Res. 1997, 30, 43-49; Nevill, S. M.; Pincock, J. A. Can. J. Chem. 1997, 75, 232-247.
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10. -3) in methanol with 313 nm light increases the composition of (4a + 5a) relative to 6a by a factor of 2.2 at 19.0% conversion implies that the N-O bond cleavage in the excited singlet-state 1a and 1c takes place by different mechanisms.
11. 8. Sakurai, T.; Obana, T.; Inagaki, T.; Inoue, H. J. Chem. Soc., Perkin Trans. 2, 1989, 535-538; Sakurai, T.; Murakata, Y.; Inoue, H. J. Chem. Soc., Perkin Trans. 2, 1990, 499-503.
12. 8. Sakurai, T.; Obana, T.; Inagaki, T.; Inoue, H. J. Chem. Soc., Perkin Trans. 2, 1989, 535-538; Sakurai, T.; Murakata, Y.; Inoue, H. J. Chem. Soc., Perkin Trans. 2, 1990, 499-503.
13. 2: C, 81.21 (81.13); H, 4.65 (4.67); N, 4.30% (4.18%).
14. 3) δ 3.55 (s, 3H), 5.44 (s, 2H), 7.47 (dd, 2H, J= 6.4, 8.5 Hz), 7.55 (dd, 2H, J= 6.4, 8.5 Hz), 8.02 (d, 2H, J= 8.5 Hz), 8.39 (d, 2H, J= 8.5 Hz), 8.47 (s, 1H). Physical and spectroscopic properties of this isolated product agreed with those of an authentic sample independently prepared from the reaction between 9-(chloromethyl)anthracene and sodium methoxide in methanol.
15. 11. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd Edn.; Marcel Dekker: New York, 1993, pp. 4-53.
16. -1 is consistent with the assumption of an intramolecular exciplex.
17. 13. Burgdorff, C.; Löhmannsröben, H.-G.; Sander, T. J. Chem. Soc., Faraday Trans., 1996, 92, 3043-3049.
18. f is the area ratio of the fluorescence band for a given reference to that for 1.
19. -3 (1b).
20. -3 (1b).