Photooxygenation of l-Alkyl-2,3-diarylcyclopropanes via Photoinduced Electron Transfer: Stereoselective Formation of 4-Alkyl-3,5-diaryl-l,2-dioxolanes and Their Conversion to 1,3-Diols

Journal of Organic Chemistry

Volumn 55, Issue 13, 1990, Pages 4079-4083

  Ichinose, Nobuyuki ^a   Mizuno, Kazuhiko ^a   Otsuji, Yoshio ^a   Tamai, Toshiyuki ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000784215     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00300a024     Document Type: Article

References (41)

1. Futamure, S.; Kusunose, S.; Ohta, H.; Kamiya, Y. J. Chem. Soc., Perkin Trans. 1 1984, 15.
2. Miyashi, T.; Takahashi, Y.; Yokogawa, K.; Mukai, T. J. Chem. Soc., Chem. Commun. 1987. 175.
3. Schaap, A. P.; Lopez, L.; Gagnon, S. D. J. Am. Chem. Soc. 1983, 105, 663.
4. Schaap, A. P.; Siddiqui, S.; Gagnon, S. D.; Lopez, L. J. Am. Chem. Soc. 1983, 105, 5149.
5. Schaap, A. P.; Siddiqui, S.; Prasad, G.; Rahman, A. F. M.; Oliver, J. F. J. Am. Chem. Soc. 1984, 106, 6087.
6. Schaap, A. P.; Siddiqui, S.; Balakrishnan, P.; Lopez, L.; Gagnon, S. D. Isr. J. Chem. 1983, 23, 415.
7. Schaap, A. P.; Siddiqui, S.; Prasad, G.; Palomino, E.; Lopez, L. J. Photochem. 1984, 25, 167.
8. Schaap, A. P.; Siddiqui, S.; Prasad, G.; Palomino, E.; Sandison, M. Tetrahedron 1985, 41, 2229.
9. Schaap, A. P.; Lopez, L.; Anderson, S. D.; Gagnon, S. D. Tetrahedron Lett. 1982, 23, 5493.
10. Shim, S. C.; Song, J. S. J. Org. Chem. 1986, 51, 2817.
11. Miyashi, T.; Kamata, M.; Mukai, T. J. Am. Chem. Soc. 1987, 109, 2780.
12. Akasaka, T.: Ando, W. J. Am. Chem. Soc. 1987. 109. 1260.
13. Mizuno, K.; Kamiyama, N.; Otsuji, Y. Chem, Lett. 1983, 478.
14. Mizuno, K.; Ichinose, N.; Otsuji, Y. Chem, Lett. 1985, 445
15. Mizuno, K.; Kami-vama, N.; Ichinose, N.: Otsuii, Y. Tetrahedron 1985. 41. 2207.
16. Mizuno, K.; Murakami, K.; Kamiyama, N.; Otsuji, Y. J. Chem. Soc., Chem. Commun. 1983, 462
17. Kirschenheuter, G. P.; Griffin, G. W. J. Chem. Soc., Chem. Commun. 1983, 596.
18. Griffin, G. W.; Kirschenheuter, G. P.; Vaz, C.; Umrigar, P. P.; Lankin, D. C.; Christensen, S. Tetrahedron 1985, 41, 2081.
19. Gollnick, K.; Schnatterer, A. Tetrahedron Lett. 1984. 25. 2735.
20. Feldman, K. S.; Simpson, R. E.; Parvez, M. J. Am. Chem. Soc. 1986. 108. 1328 and references cited therein.
21. The relative configurations of la and 3a are denoted by adding the prefix r (for reference) to the lowest number locant and the prefixes c (for cis) or t (for trans) as appropriate to the number locants: Fletcher, J. H.; Dermer, O, C.; Fox, R. B. Nomenclature of Organic Compounds; American Chemical Society: Washington. DC. 1974: p 112.
22. Irradiation of la and 2a in acetonitrile in the absence of 02 gave a photostationary mixture consisting of la and 2a in an 8:2 ratio as a result of the photoisomerization of the starting cyclopropanes. However, the other isomer, r-l,c-2-bis(4-methoxyphenyI)-c-3-methylcyclopropane, was not detected in an appreciable amount in this photoisomerization reaction.
23. The thermal decomposition of 3a in refluxing benzene for 30 min gave 4-methoxybenzaldehyde and 1-(4-methoxyphenyl)propanone in a 1:1 ratio.
24. Compounds 6d,e were unstable in protic solvents. They transformed gradually in methanol to complex mixtures containing 4-substituted benzaldehvde derivatives and 4-substituted phenylpropenes.
25. The hydrogenolysis of 3,5-diaryl-l,2-dioxolanes obtained by the photooxygenation of 1,2-diary lcyclopropanes in a similar manner afforded the corresponding l,3-diaryl-l,3-diols as a mixture of their 1,3-threo and 1,3-erythro isomers in quantitative yields. The ratios of the stereoisomers (threo:erythro = 3:7) in these 1,3-diols were also identical with those of the stereoisomers (cis:trans = 7:3) in the starting 1,2-dioxolanes.
26. Barluenga, J.; Resa, J. G.; Olano, B.; Fustero, S. J. Org. Chem. 1987. 52. 1425.
27. For the 1H and 13C NMR spectral data of 6a—e and the related 1,3-diols, see: Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009.
28. Bloch, R.; Gilbert, L.; Girard, C. Tetrahedron Lett. 1988, 29, 1021.
29. Ariamala, G.; Balasubramanian, K. K. Tetrahedron Lett. 1988, 29, 3335.
30. Gilchrist, T. L.; Stannard, A. M. Tetrahedron Lett. 1988, 29, 3586.
31. Feldman, K. S.: Simpson, R. E. Tetrahedron Lett. 1989. 30. 6985.
32. A similar salt effect was reported in the other systems: Evans, T. R.; Wake, R. W.; Sifan, M. M. Tetrahedron Lett. 1973, 701.
33. Mizuno, K.; Ichinose, N.; Tamai, T.; Otsuji, Y. Tetrahedron Lett. 1985, 26, 5823.
34. Lewis, F. D.; Petsce, J. R.; Oxman, J. D.; Nepras, M. J. J. Am. Chem. Soc. 1985, 107, 203.
35. Saito, I.; Ikehira, H.; Kasatani, R.; Watanabe, M.; Matsuura, T. J. Am. Chem. Soc. 1986, 108, 3115.
36. Pac, C.; Fukunaga, T.; Go-an, Y.; Sakae, T.; Yanagida, S. J. Photochem. Photobiol. 1987, 41, 37.
37. Rehm, D. Weller, A. Isr. J Chem. 1970. 8, 259.
38. Goodson, B.; Schuster, G. B. Tetrahedron Lett. 1986, 27, 3123.
39. Eriksen, J.; Foote, C. S. J. Phys. Chem. 1978, 82, 2659.
40. Beach, S. G.; Turnbull, J. H.; Wilson, W. J. Chem. Soc. 1952, 4686.
41. Hixson, S. S.; Garrett, D. W. J. Am. Chem. Soc. 1974, 96, 4872.