Photoinduced electron transfer reactions of cyclopropanone acetal with conjugated enones in the presence of a redox-type photosensitizer

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1833-1836

  Abe, Manabu ^a   Nojima, Masatomo ^a   Oku, Akira ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HYDROXYACID; OXOACID; PHOTOSENSITIZING AGENT;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029917805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00155-4     Document Type: Article

References (18)

1. a) Jurriard, M.; Chanon, M. Chem. Rev. 1983, 83, 425.
2. b) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
3. a) Müller, F.; Mattay, J. Chem. Rev. 1993, 93, 99.
4. b) Mizuno, K.; Otsuji, Y. Top. Curr. Chem. 1994, 169, 301.
5. c) Mariano, P. S. Acc. Chem. Res. 1993, 25, 233.
6. a) Abe, M.; Oku, A. Tetrahedron Lett. 1994, 35, 3551.
7. b) Oku, A.; Abe, M.; Iwamoto, M. J. Org. Chem. 1994, 59, 7445.
8. c) Abe, M.; Oku, A. J. Chem. Soc., Chem. Commun. 1994, 1673.
9. d) Abe, M.; Oku, A. J. Org. Chem. 1995, 60, 3065.
10. Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1977, 99, 7360.
11. a) Majima, T.; Pac, C.; Sakurai, H. J. Am. Chem. Soc. 1981, 103, 4499.
12. b) Mizuno, K.; Takahashi, N.; Nishiyama, T.; Inoue, H. Tetrahedron. Lett. 1995, 36, 7463.
13. Conjugated enones in excited states are intermolecularly unreactive as a consequence of rapid cis-trans photoisomerization in solution.11 In fact, the PET reactions between 1 and 2a did not take place under direct irradiation. Therefore, a redox-type photosensitizer is required to facilitate the PET reaction.
14. For the stabilization of radical ions by metal salts, see: Mizuno, K.; Hiromoto, Z.; Ohnishi, K.; Otsuji, Y. Chem. Lett. 1983, 1059, and references cited theirin.
15. Stewart, J. J. P. J. Comp. Chem. 1989,10, 209.
16. See also: Past, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259.
17. The intervention of both metal stabilized-radical anion 7 and ring-opened radical cation 8 possessing a silyl group was suggested in the photoreaction with carbonyl compounds.3d
18. Egerton, P. L.; Hyde, E. M.; Trigg, J.; Payne, A.; Beynon, P.; Mijovice, M. V.; Reiser, A. J. Am. Chem. Soc. 1981, 103, 3859