Isomerisation of 2,2-dimethyl dimedone to (D,L) cis-chrysanthemic acid

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3871-3874

  Krief, Alain ^a   Lorvelec, Guillaume ^a   Jeanmart, Stephane ^a,b  

^a UNIVERSITY OF NAMUR   (Belgium)

^b Fonds Pour Form Rech Dans l'I   (Belgium)

Author keywords

Bamford Stevens reaction; Cyclopropanes; Hydrazones; Olefin bromination

Indexed keywords

5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; ALKENE; CYCLOPROPANE; HYDRAZONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERISM; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034697536     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00542-6     Document Type: Article

References (19)

1. Krief, A.; Surleraux, D.; Frauenrath, H. Tetrahedron Lett. 1988, 29, 6157-6160.
2. (b) Krief, A.; Surleraux, D.; Dumont, W.; Pasau, P.; Lecomte, Ph. Pure Appl. Chem. 1990, 62, 1311-1318.
3. (c) Krief, A.; Surleraux, D. Synlett 1991, 4, 273-275.
4. (d) Krief, A.; Surleraux, D.; Robson, M. J. Synlett 1991, 4, 276-278.
5. (e) Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292.
6. Krief, A. In Stereocontrolled Organic Synthesis. A 'Chemistry for the 21st Century' Monograph; Trost, B. M., Ed. International union of pure and applied chemistry. Blackwell Scientific, 1994; pp. 337-397.
7. Grob, C. A.; Schiess, P. W. Angew. Chem., Int. Ed. Engl. 1967, 6, 1-15.
8. (b) Grob, C. A. Angew. Chem., Int. Ed. Engl. 1969, 8, 535-546.
9. Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735-4790.
10. (b) Shapiro, R. H. Org. React. 1976, 23, 405-507.
11. Gaoni, Y.; Wenkert, E. J. Org. Chem. 1966, 31, 3809-3814.
12. Schaltegger, A.; Bigler, P. Helv. Chim. Acta. 1986, 69, 1666-1670.
13. Friedman, L.; Litle, R. L. Org. Synth. 1960, 40, 93-95.
14. Under other conditions the bis-tosylhydrazone is formed concommitantly (conditions, dimethyl dimedone:monotosylhydrazone:bis-tosylhydrazone ratio (1% HCl, ethanol, reflux, 0.5 h, 8:54:36; benzene, 20°C, 4 h, 68:27:5; THF, 20°C, 4 h, 33:33:33; methanol, 20°C, 4 h, 30:57:13).
15. Zeile, K.; Meyer, H. Chem. Ber. 1949, 82, 275-285.
16. Ollevier, T. PhD Thesis, Facultés Universitaires Notre-Dame de la Paix, Namur, 1997.
17. (b) Ollevier, T., unpublished results.
18. Musser, A. K.; Fuchs, P. L. J. Org. Chem. 1982, 47, 3121-3131.
19. Paquette, L. A.; Kuhla, D. E.; Barrett, J. H.; Haluska, R. J. J. Org. Chem. 1969, 34, 2866-2878.