Photochemical formation of 1,5-diketones from dibenzoylmethane and some quinones

Bulletin of the Korean Chemical Society

Volumn 20, Issue 5, 1999, Pages 531-534

  Kim, Sung Sik ^b   Lim, Jin Sun ^b   Lee, Jong Myung ^b   Shim, Sang Chul ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Chonbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DIBENZOYLMETHANE DERIVATIVE; DIKETONE; KETONE DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; IRRADIATION; KOREA; PHOTOCHEMISTRY; SYNTHESIS;

EID: 0000117077     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. Laird, T. In Comprehensive Organic Chemistry; Stoddart, J. F., Ed.; Pergamon Press: 1979; Vol. 1, p 1213.
2. Maruyama, K.; Osuka, A. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons, Inc.: New York, 1988; Part 1, Chapter 13, p 759.
3. Kim, S. S.; Yu, Y. H.; Shim, S. C.; Cho, I. H. Tetrahedron Lett. 1994, 35(48), 9039.
4. Kim, S. S.; Kim, A. R.; O, K. J.; Yoo, D. J.; Shim, S. C. Chemistry Letts. 1995, 787.
5. Weedon, A. C. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: 1995; chapter 54.
6. (a) Kim, A. R.; Kim, K. J.; Shim, S. C.; Kim, S. S. Bull. Korean Chem. Soc. 1997, 18(10), 1125.
7. (b) For the photoaddition of dibenzoylmethane to o-quinones, see Chang, J. A.; Kim, A. R.; Kim, S. S. Bull. Korean Chem. Soc. 1998, 19(9), 917.
8. -1; Mass (EI) m/e 220 (M).
9. Gano, J. Tetrahedron Lett. 1969, 2549.
10. Duhaime, R. M.; Lombardo, D. A.; Skinner, I. A.; Weedon, A. C. J. Org. Chem. 1985, 50, 873.
11. Such two isomeric adducts, i.e., oxetane and cyclobutane, were also found in the photoaddition of 1,4-naphthoquinone to 1,4-diethynylbenzene. For this reaction, see Kim, S. S.; O. K. J.: Shim, S. C. Bull. Korean Chem. Soc. 1994, 15(4), 270.
12. MM2 calculation was carried out using CambridgeSoft Chem 3D 4.0 for Windows and Macintosh program, by considering energy terms such as stretch, bend, stretch-bend, torsion, non-1,4 van der Waals, 1,4 van der Waals, and dipole/dipole.