One-step preparation of symmetrical 1,4-diketones from α-halo ketones in the presence of Zn-I2 as a condensation agent

Synthesis

Volumn , Issue 11, 2004, Pages 1750-1754

  Ceylan, Mustafa ^a   Gürdere, M Burcu ^a   Budak, Yakup ^a   Kazaz, Cavit ^b   Seçen, Hasan ^b  

^a GAZIOSMANPASA UNIVERSITY   (Turkey)

^b ATATÜRK UNIVERSITY   (Turkey)

Author keywords

1,4 Diketones; Zinc; bromoketones

Indexed keywords

AROMATIC COMPOUNDS; CONDENSATION; REACTION KINETICS; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

CONDENSATION PRODUCTS; MECHANISTIC PATHWAY;

KETONES;

1,4 DIKETONE; 1,4 DIPHENYLBUTANE 1,4 DIONE DERIVATIVE; 3 CHLOROPENTANE 2,4 DIONE; 3,4 DIACETYLHEXANE 2,5 DIONE; ACETOPHENONE DERIVATIVE; HALOKETONE; IODINE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS; WURTZ REACTION;

EID: 4043143083     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829118     Document Type: Article

References (32)

1. Ellison, R. A. Synthesis 1973, 397.
2. Bosshard, P.; Eugster, C. H. Adv. Heterocycl. Chem. 1966, 77, 377.
3. Hoeve, W. T.; Wynberg, H.; Havinga, E. E.; Meijer, E. W. J. Am. Chem. Soc. 1991, 113, 5887.
4. Sato, T.; Okazaki, H.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1988, 110, 5209.
5. Severin, T.; Koenig, D. Chem. Ber. 1974, 107, 1499.
6. Ballini, R.; Bartoli, G. Synthesis 1993, 965.
7. Moriarty, R.; Prakash, O.; Duncan, M. P. J. Chem. Soc., Perkin Trans. 1 1987, 559.
8. Stetter, H.; Jonas, F. Chem. Ber. 1981, 114, 564.
9. Stetter, H.; Schreckenberg, M. Chem. Ber. 1974, 107, 2453.
10. Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
11. Stetter, H.; Hilboll, G.; Kuhlmann, H. Chem. Ber. 1979, 112, 84.
12. Koutek, B.; Pavlickova, L.; Soucek, M. Collect. Czech. Chem. Commun. 1974, 39, 192.
13. Chiu, P. K.; Sammes, M. P. Tetrahedron 1988, 44, 3531.
14. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrel, R. J. Am. Chem. Soc. 1963, 85, 207.
15. (a) Yasuda, M.; Katoh, Y.; Shibata, I.; Baba, A.; Matsuda, H.; Sonoda, N. J. Org. Chem. 1994, 59, 4386.
16. (b) Yasuda, M.; Tsuji, S.; Shibata, I.; Baba, A. J. Org. Chem. 1997, 62, 8282.
17. Kel'in, A. V.; Kulinkovich, O. G. Synthesis 1996, 330.
18. Natali, N. M.; Kel'in, A. V.; Kulinkovich, O. G. Synthesis 2000, 1259.
19. Ghera, E.; Perry, D. H.; Shoua, S. J. Chem. Soc., Chem. Commun. 1973, 858.
20. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed., Part B; Plenum: New York, 1990, 260.
21. Kowalski, C. J.; Haque, M. S. J. Org. Chem. 1985, 50, 5140.
22. Lutz, R. E.; Allison, R. K.; Ashburn, G.; Bailey, P. S.; Clark, M. T.; Codington, J. F.; Deinet, A. J.; Freek, J. A.; Jordan, R. H.; Leake, N. H.; Martin, T. A.; Nicodemus, K. C.; Rowlett, R. J. Jr.; Shearer, N. H. Jr.; Smith, J. D.; Wilson, J. W. III J. Org. Chem. 1947, 12, 617.
23. Cowper, R. M.; Davidson, L. H. Org. Synth. Coll. Vol. II; Wiley: New York, 1943, 480.
24. Uff, B. C.; Maghami, G. G.; Budharm, R. S.; Wilson, C. L.; Apatu, J. O. J. Heterocycl. Chem. 1989, 26, 571.
25. Stetter, H.; Bender, H. J. Chem. Ber. 1981, 114, 1226.
26. Takahashi, K.; Matsuzaki, M.; Ogura, K.; Iida, H. J. Org. Chem. 1983, 48, 1909.
27. Xiao, G.; Kumar, A.; Li, K.; Rigl, C. T.; Bajic, M.; Davis, T. M.; Boykin, D. W.; Wilson, W. D. Bioorg. Med. Chem. 2001, 9, 1097.
28. Barba, F.; Velasco, M. D.; Guirado, A. Synthesis 1984, 593.
29. Huang, J. T.; Su, T. L.; Watanabe, K. A. J. Org. Chem. 1991, 56, 4811.
30. Alper, H.; Keung, E. C. H. J. Org. Chem. 1972, 37, 2566.
31. Suginome, H. J. Org. Chem. 1958, 23, 1044.
32. Gevorkyan, A. A.; Arakelyan, A. S.; Barsegyan, S. V.; Petrosyan, K. A.; Panosyan, G. A. Russ. J. Org. Chem. 2003, 39, 1204.