Mechanistic and synthetic aspects of the reaction of γ-halogeno-α,β-unsaturated ketones and esters with simple trialkyl phosphites

Organic and Biomolecular Chemistry

Volumn 1, Issue 16, 2003, Pages 2966-2972

  Waszkuć, Wieslaw ^a   Janecki, Tomasz ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHY; DISTILLATION; ESTERS; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS COMPOUNDS; STEREOCHEMISTRY; STRUCTURE (COMPOSITION); SUBSTRATES;

CYCLOPROPYLPHOSPHONATE; DIENYLPHOSPHATE; DIESTER; KETOESTER; KETOVINYLPHOSPHONATE; PHOSPHORYLATION; TRIALKYL PHOSPHITE;

SYNTHESIS (CHEMICAL);

EID: 0041317591     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b305717h     Document Type: Article

References (21)

1. J. F. Allen and O. H. Johnson, J. Am. Chem. Soc., 1955, 77, 2871.
2. L. A. Antokhina and P. I. Alimov, Izv. Akad. Nauk. SSSR, Ser. Khim., 1968, 180.
3. N. A. Mukamienova, E. N. Cherezova, L. N. Iamalieva, S. V. Koliesov, K. S. Minsker and P. A. Kirpichnikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1106.
4. D. M. Malenko, N. V. Simurova and A. D. Sinica, Zh. Obshch. Khim., 1988, 63, 1921.
5. Ch. V. Stevens, G. Van Heecke, C. Barbero, K. Patora, N. De Kimpe and R. Verhe, Synlett, 2002, 1089.
6. E. Kiehlmann, P-W. Loo, B. C. Menon and N. Mc Gillivray, Can. J. Chem., 1971, 49, 2964.
7. E. M. Gaydou, Can. J. Chem., 1973, 51, 3412.
8. 31P-element couplings: proton-phosphorus coupling, in Phosphorus-31 NMR spectroscopy in stereochemical analysis. Ed. J. G. Verkade, L. D. Quinn, VCH Publishers, Inc., Deerfield Beach Florida, 1987, p. 366.
9. I. Petneházy, G. Szakál, L. Toke, H. R. Hudson, L. Powroznyk and Ch. J. Cooksey, Tetrahedron, 1983, 39, 4229.
10. F. Ramirez, J. F. Pilot, O. P. Madan and C. P. Smith, J. Am. Chem. Soc., 1968, 90, 1275.
11. D. Goŕenstein, J. Am. Chem. Soc., 1970, 92, 644.
12. A. M. Modro and T. A. Modro, Can. J. Chem., 1988, 66, 1541.
13. S. Tsuboi, Y. Ishiguro and A. Takeda, Bull. Chem. Soc. Jpn., 1974, 47, 1673.
14. S. Tsuboi, T. Uno and A. Takeda, Chem. Lett., 1978, 1325.
15. J. Liu, E. N. C. Browne and P. R. Pednekar, Can. J. Chem., 1982, 60, 921.
16. H. Eckert and I. Ugi, Liebigs Ann. Chem., 1979, 278.
17. M. L. Wolfrom, J. Radell and R. M. Husband, J. Org. Chem., 1957, 22, 329.
18. H. J. Dauben Jr. and L. L. Mc Coy, J. Org. Chem., 1959, 24, 1577.
19. R. Verhe, N. De Kimpe, D. Courtheyn, L. De Buye and N. Schamp, Tetrahedron, 1982, 38, 3649.
20. J. Mc Intosh and I. E. E. Hayes, Can. J. Chem., 1987, 65, 110.
21. Values taken from the spectra of the mixture of isomers.