Oxidative Synthesis of α,β-Unsaturated Ketone from α-Iodo Ketone Using Peracid

Synthesis

Volumn , Issue 2, 2004, Pages 202-204

  Horiuchi, C Akira ^a   Ji, Shun Jun ^b   Matsushita, Masatoshi ^a   Chai, Wen ^a  

^a RIKKYO UNIVERSITY   (Japan)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

Elimination reaction; Oxidation; , unsaturated ketone; iodo ketone

Indexed keywords

BENZENE; ORGANIC ACIDS; OXIDATION; SYNTHESIS (CHEMICAL);

OXIDATIVE SYSTHESIS; PERACID;

KETONES;

BENZOIC ACID DERIVATIVE; IODINE DERIVATIVE; KETONE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; ELIMINATION REACTION; OXIDATION; REACTION ANALYSIS;

EID: 1242296079     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44371     Document Type: Article

References (32)

1. Dauben, W. G.; Lorber, M.; Fullerton, D. S. J. Org. Chem. 1969, 54, 3581.
2. (a) Jones, R. N.; Ramsay, D. A.; Herling, E.; Dobriner, K. J. Am. Chem. Soc. 1952, 74, 2828.
3. (b) Kuehne, M. E. J. Am. Chem. Soc. 1961, 83, 1492.
4. (c) Warnhoff, E. W. J. Org. Chem. 1962, 27, 4587.
5. Reich, H. J.; Reich, I. L.; Renga. J. M. J. Am. Chem. Soc. 1973, 95, 5813.
6. (a) Braude, E. A.; Brook, A. G.; Linsted, R. P. J. Chem. Soc. 1954, 3569.
7. (b) Burn, D.; Kirk, D. N.; Petrow, V. Proc. Chem. Soc. 1960, 14.
8. Jerussi, R. A.; Speyer, D. J. Org. Chem. 1966, 31, 3199.
9. (a) Pearson, A. J.; Chen, Y. S.; Hsu, S. Y.; Ray, T. Tetrahedron Lett. 1984, 25, 1235.
10. (b) Pearson, A. J.; Chen, Y. S.; Hang, G. R.; Hsu, S. Y.; Ray, T. J. Chem. Soc., Perkin Trans. 1 1985, 267.
11. (c) Chidambaram, N.; Chandrasekaran, S. J. Org. Chem. 1987, 52, 5048.
12. (d) Miller, R. A.; Li, W.; Humphrey, G. R. Tetrahedron Lett. 1996, 37, 3429.
13. (e) Salvador, J. A. R.; Sa e Melo, M. L.; CamposNeves, A. S. Tetrahedron Lett. 1997, 38, 119.
14. Kirk, D. N.; Hartshorr, M. P. Steroid Reaction Mechanisms; Elsevier: Amsterdam, London, New York, 1968, 109-110.
15. (a) Ogata, Y.; Aoki, K. J. Org. Chem. 1969, 34, 3974.
16. (b) Ogata, Y.; Aoki, K. J. Org. Chem. 1969, 34, 3978.
17. Beeley, N. R. A.; Sutherland, J. K. J. Chem. Soc., Chem. Commun. 1977, 321.
18. Reich, H. J.; Peake, S. L. J. Am. Chem. Soc. 1978, 100, 4888.
19. (a) Horiuchi, C. A.; Kiji, S. Chem. Lett. 1988, 31.
20. (b) Horiuchi, C. A.; Kiji, S. Bull. Chem. Soc. Jpn. 1997, 70, 421.
21. (c) Horiuchi, C. A.; Ochiai, K.; Fukunishi, H. Chem. Lett. 1994, 185.
22. (d) Horiuchi, C. A.; Takahashi, E. Bull. Chem. Soc. Jpn. 1994, 67, 271.
23. Ji, S.-J.; Takahashi, E.; Takahashi, T. T.; Horiuchi, C. A. Tetrahedron Lett. 1999, 40, 9263.
24. Ji, S.-J.; Horiuchi, C. A. Bull. Chem. Soc, Jpn. 2000, 73, 1645.
25. 9OI [M]: 271.9699; found: 271.9734.
26. Djerassi, C.; Scholz, C. R. J. Am. Chem. Soc. 1947, 69, 2404.
27. (a) Kharasch, M. S. J. Am. Chem. Soc. 1958, 80, 756.
28. (b) Ager, D. J.; Fleming, I. J. Chem. Soc., Chem. Commun. 1978, 177.
29. (c) Garbisch, E. W. J. Org. Chem. 1965, 30, 2109.
30. (d) Eaton, P. E.; Lin, K. J. Am. Chem. Soc. 1964, 86, 2087.
31. (e) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137.
32. (f) Wilds, A. L.; Djerassi, C. J. Am. Chem. Soc. 1946, 68, 1712.