A novel photorearrangement of 1,3-diketonatoborinate: A photoinduced intramolecular alkylation on a conjugated carbonyl system

Canadian Journal of Chemistry

Volumn 77, Issue 8, 1999, Pages 1374-1383

  Ishiyama, Jun Ichi ^a   Chow, Yuan L ^b  

^a SIMON FRASER UNIVERSITY   (Canada)

^b FUKUSHIMA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

Alkylborane addition; B C bond homolytic scission; Borinate photochemistry; Boronate intermediates; Charge transfer absorption

Indexed keywords

9 BORABICYCLO[3,3,1]NONANE; ACETIC ACID; BORINIC ACID DERIVATIVE; DIKETONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BOND; CONJUGATION; DEHYDRATION; OXIDATION; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0033306731     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-139     Document Type: Article

References (30)

1. (a) K. Okada, Y. Hosoda, and M. Oda. J. Am. Chem. Soc. 108, 321 (1986);
2. (b) Tetrahedron Lett. 27, 6213 (1986).
3. K. Utimoto, T. Tanaka, and H. Nozaki. Tetrahedron Lett. 1167 (1972).
4. K. Okada, H. Inokawa, and M. Oda. Tetrahedron Lett. 30, 4395 (1989).
5. (a) S. Chatterjee, P.D. Davis, P. Gottschalk, M.E. Kurz, B. Sauerwein, X. Yang, and G.B. Schuster. J. Am. Chem. Soc. 112, 6329 (1990);
6. J.D. Wilkey and G.B. Schuster. J. Am. Chem. Soc. 113, 2149 (1991).
7. (a) Y.L. Chow and X.-E. Cheng. Can. J. Chem. 69, 1331 (1991); 69, 1575 (1991);
8. (a) Y.L. Chow and X.-E. Cheng. Can. J. Chem. 69, 1331 (1991); 69, 1575 (1991);
9. (b) Y.L. Chow, S.S. Wang, C.I. Johansson, and Z.-L. Liu. J. Am. Chem. Soc. 118, 11725 (1996).
10. (a) Y.L. Chow, Y.-H. Zhang, M.X. Zhang, and A. Rassat. Chem. Phys. Lett. 272, 471 (1997);
11. (b) H.-D. Ilge, E. Birckner, D. Fassler, D. Kozmenko, M.D. Kuz'min, and H. Hartmann. J. Photochem. 32, 177 (1986).
12. J. Yoon and A.W. Czarnik. J. Am. Chem. Soc. 114, 3874 (1992).
13. (a) M.F. Hawthorne and M. Reintjes. J. Org. Chem. 30, 3851 (1965);
14. (b) R. Koster and G.W. Rotermund. Liebigs Ann. Chem. 689, 40 (1965);
15. (c) L.H. Toporcer, R.E.Dessy, and S.I.E. Green. Inorg. Chem. 4, 1649 (1965);
16. (d) R. Boese, R. Koster, and M. Yalpani. Chem. Ber. 118, 670 (1985).
17. (a) N.J. Turro. Modern molecular photochemistry. Benjamin-Cummings, Menlo Park, Calif. 1978;
18. (b) J. Gersdorf, J. Mattay, and H. Gorner. J. Am. Chem. Soc. 109, 1203 (1987);
19. (c) Y.L. Chow, M. Vanossi, and S.-S. Wang. J. Photochem. Photobiol. A: 88, 125 (1995).
20. K.L. Pillay, K. Hanaya, and Y.L. Chow. Can. J. Chem. 53, 3022 (1975).
21. Y.L. Chow and X. Liu. Can. J. Chem. 69, 1261 (1991).
22. (a) K. Negishi and H.C. Brown. J. Am. Chem. Soc. 95, 6757 (1973);
23. (b) P. Jacob III. J. Organomet. Chem. 156, 101 (1978).
24. K.U. Ingold and B.P. Roberts. Free-radical substitution reactions. John Wiley & Sons, New York. 1971. pp. 46-62.
25. (a) J. Grotewold and E.A. Lissi. Chem. Commun. 1367 (1968);
26. (b) J. Chem. Soc. (B), 264 (1968).
27. L.H. Toporcer, D.E. Dessy, and S.I.E. Green. J. Am. Chem. Soc. 87, 1236 (1965).
28. (a) W. Gerrard, M.F. Lappert, and R. Shafferman. J. Chem. Soc. 3648 (1958);
29. (b) E.W. Abel, W. Gerrard, and M.F. Lappert. J. Chem. Soc. 5051 (1957); 1451 (1958).
30. (b) E.W. Abel, W. Gerrard, and M.F. Lappert. J. Chem. Soc. 5051 (1957); 1451 (1958).