A Convenient Synthesis of 2-Chlorophenyl Methylidene-5,5-dimethylcyclopentanone, a Key Intermediate for a Potent Fungicide against Botrytis cinera

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3793-3794

  Quesnel, Yannick ^a   Bidois Sery, Laure ^a   Poirier, Jean Marie ^a   Duhamel, Lucette ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLOROPHENYL METHYLIDENE 5,5 DIMETHYLCYCLOPENTANONE; FUNGICIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; FUNGICIDAL ACTIVITY; METHODOLOGY; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032577513     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972199c     Document Type: Article

References (27)

1. (a) Mugnier, J.; Greiner, A.; Hutt, J.; Pepin, R. (Rhône Poulenc Agrochimie) French patent 2 662 911 (12/06/90).
2. (b) Hutt, J.; Mugnier, J.; Pepin, R.; Greiner, A. (Rhône Poulenc Agrochimie), European patent 378 953 (29/12/88).
3. (a) Haller, A.; Cornubert, R. Bull Soc. Chim. Fr. 1926, 39, 1724.
4. (b) Bouveault, L.; Locquin, R. Bull. Soc. Chim. Fr. 1908, 3, 437.
5. (c) House, H. O.; Trost, B. M. J. Org. Chem. 1965, 30, 2505.
6. (a) Gault, F. G.; Germain, J. E.; Conia, J. M. Bull. Soc. Chim. Fr. 1957, 1064.
7. (b) House, H. O.; Kramar, V. J. Org. Chem. 1963, 28, 3362.
8. (c) Coates, R. M.; Sowerby, R. L. J. Am. Chem. Soc. 1971, 93, 1027.
9. (a) Blanc, G. Bull. Soc. Chim. Fr. 1865, 3, 780.
10. (b) Blanc, G. Bull. Soc. Chim. Fr. 1908, 3, 780.
11. (c) Wilcox, C. F., Jr.; Mesirov, M. J. Org. Chem. 1960, 25, 1841.
12. (d) Meerwein, H.; Unkel, W. Ann. 1910, 376, 152.
13. (e) King, F. E.; King, T. J.; Topliss, J. G. J. Chem. Soc. 1957, 919.
14. (f) Kopecky, K. R.; Levine, C. Can. J. Chem. 1981, 59, 3273.
15. Larchevêque, M.; Debal, A.; Cuvigny, Th. J. Organomet. Chem. 1975, 87, 25.
16. (b) Larchevêque, M.; Debal, A.; Cuvigny, Th. Bull. Soc. Chim. Fr. 1974, 1710.
17. Fairly, D. P.; Bosnich, B. Organometallics 1988, 7, 936.
18. (a) Bartlett, P. D.; Bavley, A. J. Am. Chem. Soc. 1938, 60, 2416.
19. (b) Conley, R. T. Rec. Trav. Chim. 1962, 81, 198.
20. (c) Krief, A.; Laboureur, J. L.; Dumont, W. Tetrahedron Lett. 1987, 28, 1549.
21. Duhamel, P.; Cahard, D.; Quesnel, Y.; Poirier, J. M. J. Org. Chem. 1996, 61, 2232.
22. Duhamel, P.; Cahard, D.; Poirier, J. M. J. Chem. Soc., Perkin Trans, 1 1993, 2509.
23. Fleming, I.; Higgins, D.; Lawrence, N. J.; Thomas, A. P. J. Chem. Soc., Perkin Trans, 1 1992, 24, 3331.
24. The transformation of initial potassium aldolate into enone 3 can occur via the following equilibrium: chemical equation presented.
25. (a) Cazeau, P.; Moulines, F.; Laporte, O.; Duboudin, F. J. Organomet. Chem. 1980, 201, 2075.
26. (b) Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunoguès, J. Tetrahedron 1987, 43, 2085.
27. House, H. O.; Czuba, L. Z.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324.