X. Wang, Y. Zhang / Tetrahedron Letters 43 (2002) 5431–5433
5433
system (entries 5 and 6). However, the expected deoxy-
genative coupling product was not obtained with the
1,2-diketone as the major product and the a-ketol
compound as by-product.
6. Souppe, J.; Namy, J.-L.; Kagan, H. B. Tetrahedron Lett.
1984, 25, 2869.
7. Oakwood, T. S.; Weisberger, C. A. Org. Synth. 1955, 3,
112.
8. Katritzky, A. R.; He, H. Y.; Suzuki, K. J. Org. Chem. 2000,
65, 8210.
In conclusion, with good yields, mild reaction condi-
tions as well as easily accessible starting materials, the
present work may provide a useful method for the
preparation of 1,2-diketones.12
9. (a) Evans, D. F.; Fazakerley, G. V.; Phillips, R. F. J. Chem.
Soc. (A) 1971, 1931; (b) Wipf, P.; Venkatraman, S. J. Org.
Chem. 1993, 58, 3455.
10. A relevant report concerned the PhCH2CO radical, which
is known for its rapid decarbonylation. See: (a) Lunazzi,
L.; Ingold, K. U.; Scalano, J. C. J. Phys. Chem. 1983, 87,
529; (b) Turro, N. J.; Gold, I. R.; Baretz, B. H. J. Phys.
Chem. 1983, 87, 531.
Acknowledgements
11. Ogawa, A.; Takami, N.; Sekiguehi, M. J. Am. Chem. Soc.
We are grateful to the National Natural Science Foun-
dation of China (Project No. 29872010) and the NSF of
Zhejiang province for financial support.
1992, 114, 8729.
12. Typical physical data of compounds 2e, 2h and 3 are listed.
Compound 2e, bis(4-iodophenyl)ethanedione, mp 243–
1
245°C. wmax: 3066, 1664 (CꢀO), 1579 (Ar) cm−1. H NMR
(400 MHz, DMSO-d6): 8.03 (4H, d, J=8.43 Hz, ArH), 7.67
(4H, d, J=8.44 Hz, ArH). Compound 2h, bis(4-diethyl-
aminophenyl)ethanedione, mp 85–87°C. wmax: 2972, 2933,
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1
2902, 2871, 1645 (CꢀO), 1585, 1546, 1527 cm−1. H NMR
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