Donor-acceptor binary photocatalysis system illustrated by the intramolecular cyclization of a cyclopropanone acetal tethered to cyclohexen- 2-one

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 3, 1999, Pages 511-517

  Oku, Akira ^a   Miki, Toshiyuki ^a   Abe, Manabu ^a   Ohira, Masatoshi ^a   Kamada, Tohru ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; CYCLOHEXEN 2 ONE; CYCLOPROPANONE ACETAL; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; ELECTRON TRANSPORT; IRRADIATION; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PHOTOACTIVATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032949307     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.511     Document Type: Article

References (52)

1. A number of studies have been reported on the donor character and synthetic use of cyclopropanes. For the references, see: M. Abe and A. Oku, J. Org. Chem., 60, 3065 (1995), which cites 32 papers.
2. A. Oku, M. Iwamoto, and M. Abe, Tetrahedron Lett., 33, 7169 (1992).
3. M. Abe and A. Oku, Tetrahedron Lett., 35, 3551 (1994).
4. A. Oku, M. Abe, and M. Iwamoto, J. Org. Chem., 59, 7445 (1994).
5. M. Abe and A. Oku, J. Chem. Soc., Chem. Commun., 1994, 1673.
6. S. Aoki, T. Fujita, E. Nakamura, and I. Kuwajima, J. Am. Chem. Soc., 103, 7675 (1981).
7. a) E. Nakamura and I. Kuwajima, J. Am. Chem. Soc., 99, 7360 (1977);
8. b) E. Nakamura, H. Oshino, and I. Kuwajima, J. Am. Chem. Soc., 108, 3745 (1986);
9. c) E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, and I. Kuwajima, J. Am. Chem. Soc., 109, 8056 (1987);
10. d) T. Fujita, S. Aoki, and E. Nakamura, J. Org. Chem., 56, 2809 (1991).
11. M. Abe, M. Nojima, and A. Oku, Tetrahedron Lett., 37, 1833 (1996).
12. For example, a) F. D. Lewis, G. D. Reddy, S. Schneider, and M. Gahr, J. Am. Chem. Soc., 113, 3498 (1991);
13. b) A. J. Y. Lan, R. O. Heuckeroth, and P. S. Mariano, J. Am. Chem. Soc., 109, 2738 (1987);
14. c) R. Ahmed-Schofield and P. S. Mariano, J. Org. Chem., 52, 1478 (1987);
15. d) G. Dai-Ho and P. S. Mariano, J. Org. Chem., 53, 5113 (1988);
16. e) R. W. Kavash and P. S. Mariano, Tetrahedron Lett., 30, 4185 (1989);
17. f) J. W. Ullrich, F. T. Chiu, T. Tiner-Harding, and P. S. Mariano, J. Org. Chem., 49, 220 (1984);
18. g) F. T. Chiu, J. W. Ullrich, and P. S. Mariano, J. Org. Chem., 49, 228 (1984).
19. W. Xu, X. Zhang, and P. S. Mariano, J. Am. Chem. Soc., 113, 8863 (1991).
20. All compounds 5, 7, and 21 have a three-carbon chain which divides the cyclopropane and cyclohexenone moieties. Other homologues bearing a shorter or longer chain on irradiation did not give cyclized products but decomposed via the Norrish Type II fission to give alkenylcydopropanes.
21. a) G. Roussau and N. Slougui, Tetrahedron Lett., 24, 1251 (1983);
22. b) G. A. Molander and L. S. Harring, J. Org. Chem., 54, 3525 (1989);
23. c) S. E. Denmark and J. P. Edwards, J. Org. Chem., 56, 6974 (1991).
24. a) L. A. Paquette, D. T. Belmont, and Y. Hsu, J. Org. Chem., 50, 4667 (1985);
25. b) M. E. Krafft and R. A. Holton, Tetrahedron Lett., 24, 1345 (1983).
26. a) L. Blanco, P. Amice, and J. M. Conia, Synthesis, 1976, 194;
27. b) P. Amice, L. Blanco, and J. M. Conia, Synthesis, 1976, 194;
28. c) R. H. Reuss and A. Hassner, J. Org. Chem., 39, 1785 (1974).
29. a) P. L. Stotter and K. A. Hill, J. Org. Chem., 38, 2576 (1973);
30. b) R. Joly, J. Warnant, G. Nominé, and D. Bertin, Bull. Soc. Chim. Fr., 1958, 366.
31. 2 and solvents, was found unsuccessful (Scheme 7).
32. J. P. Marino, R. Fernández de la Pradilla, and E. Laborde, J. Org. Chem., 52, 4898 (1987).
33. a) S. Knapp, M. J. Sebastian, and H. Ramanathan, J. Org. Chem., 24, 4786 (1983);
34. b) M. Korach, D. R. Nielsen, and W. H. Rideout, Org. Synth., Coll. Vol. V, 414 (1973).
35. F. Sondheimer, C. Amendolla, and G. Rosenkranz, J. Chem. Soc., 75, 5930 (1953).
36. 2 in the photolysis of carbonyl compounds gave improved result. see: a) K. Mizuno, Z. Hiromoto, K. Ohnishi, and Y. Otsuji, Chem. Lett., 1983, 1059;
37. b) K. Mizuno, I. Nakanishi, and Y. Otsuji, Chem. Lett., 1988, 1833;
38. c) K. Mizuno, I. Nakanishi, N. Ichinose, and Y. Otsuji, Chem. Lett., 1989, 1095;
39. d) K. Mizuno and Y. Otsuji, J. Synth. Org. Chem. Jpn., 47, 916 (1989);
40. e) I. Saito, H. Ikehira, R. Kasatani, M. Watanabe, and T. Matsuura, J. Am. Chem. Soc., 108, 3115 (1986);
41. f) E. Hasegawa, M. A. Brumfield, and P. S. Mariano, J. Org. Chem., 53, 5435 (1988);
42. g) J. Mattay, G. Trampe, and J. Runsink, Chem. Ber., 121, 1991 (1988);
43. h) T. Miyashi, A. Konno, and Y. Takashi, J. Am. Chem. Soc., 110, 3676 (1988);
44. i) O. Ishitani, M. Ihama, Y. Miyauchi, and C. Pac, J. Chem. Soc., Perkin. Trans. 1, 1985, 1527. For mechanistic discussions, see also Ref. 1.
45. We use the term "catalyst" instead of "sensitizer" because these aromatic hydrocarbons activate the donor-acceptor binary systems by the electron transfer process but not by energy transfer.
46. On the basis of our previous study (Ref. 8) where the fluorescence quenching experiments (excitation at 350 nm, detection at 372 and 391 nm) for the singlet excited state of pyrene by diethyl fumarate and cyclopropanone acetal 1, respectively, proved efficient quenching only by fumarate, it is rather clear that pyrene (and presumably phenanthrene) in its singlet excited state functions as a donor in the present SET systems.
47. The cyclization systems we adopted, e.g. 5, have both donor and acceptor functionalities. Therefore, a donor-type catalyst may first activate the carbonyl moiety whereas an acceptor-type catalyst may activate the cyclopropane moiety. See also Refs. 8 and 22.
48. .- and the cation radical of 1, thus producing β-carbonyl radical 25. This effect of silyl substituents constitutes the working basis in most of our preceding studies (Refs. 1, 2, 3, 4, 5, and 8).
49. Y. J. Lee, R. Ling, P. S. Mariano, U. C. Yoon, D. U. Kim, and S. W. Oh, J. Org. Chem., 61, 3304 (1996).
50. W. Wierenga and H. I. Skulnick, Org. Synth., Coll. Vol. VII, 213 (1990).
51. .-) = -1.60 vs. SCE: S. L. Mattes and S. Farid, in "Organic Photochemistry," ed by A. Padwa, Marcel Dekker, New York (1983), Vol. 6, p. 233.
52. J. Attenburrow, A. F. B. Cameron, J. H. Chapman, R. M. Evans, B. A. Hems, A. B. A. Jansen, and T. Walker, J. Chem. Soc., 1953, 1094.