Preparation of α-ketophosphonates by a [3,3]-sigmatropoic shift of enolphosphonates

Journal of Organometallic Chemistry

Volumn 690, Issue 10, 2005, Pages 2688-2691

  Afarinkia, Kamyar ^a   Twist, Andrew J ^a   Yu, Hiu Wan ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Ketophosphonate; 3,3 Sigmatropic shift; Enolphosphonate

Indexed keywords

ALKYLATION; MIXTURES; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITIONS; PHOSPHORUS COMPOUNDS; SOLVENTS; SULFONATION;

Α-KETOPHOSPHONATES; ENOLPHOSPHONATES; NUCLEOPHILES; TRANSITION STATES;

ESTERS;

EID: 17944363879     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.10.016     Document Type: Conference Paper

References (28)

1. K. Afarinkia, and M.V. Vinader C.J. Moody Comprehensive Organic Functional Group Transformations vol. 5 1995 Pergamon London 393
2. P. Savignac, and B. Igora Modern Phosphonate Chemistry 2003 CRC Press New York 319
3. K. Afarinkia, in: R.C.F. Jones (Ed.), Comprehensive Organic Functional Group Transformations II, vol. 5, Elsevier, London, 2004 (in press)
4. T. Oshikawa, and M. Yamashita Bull. Chem. Soc. Jpn 63 1990 2728
5. R. Karaman, A. Goldblum, E. Breuer, and H.J. Leader Chem. Soc., Perkin Trans. 1 1989 765
6. M. Yamashita, M. Kojima, H. Yoshida, T. Ogata, and S. Inokawa Bull. Chem. Soc. Jpn 53 1980 1625
7. E. Breuer, A. Schlossman, M. Safadi, D. Gibson, M. Chorev, and H.J. Leader Chem. Soc., Perkin Trans. 1 1990 3263
8. E. Breuer, H. Zaher, and Z. Tashma Tetrahedron Lett. 1992 2067
9. H. Scherer, A. Hartmann, M. Regitz, B.D. Tunggal, and H. Günther Chem. Ber. 105 1972 3357
10. E. Öhler, E. Zbiral, and M. El-Badawi Tetrahedron Lett. 24 1983 5599
11. F. Hammerschmidt, and E. Zbiral Ann. Chem. 1979 492
12. D.A. Evans, J.S. Johnson, and E.J. Olhava J. Am. Chem. Soc. 122 2000 1635
13. L.A. Telan, C.-D. Poon, and S.A. Evans Jr. J. Org. Chem. 61 1996 7455
14. S. Hanessian, and P. Compain Tetrahedron 58 2002 6521
15. A. Kume, M. Fujii, M. Sekine, and T. Hata J. Org. Chem. 49 1984 2139
16. M. Sekine, M. Satoh, H. Yamagata, and T. Hata J. Org. Chem. 45 1980 4162
17. M. Fujii, K. Ozaki, M. Sekine, and T. Hata Tetrahedron 43 1987 3395
18. E. Breuer, R. Karaman, A. Goldblum, and H. Leader J. Chem. Soc., Perkin Trans. 2 1988 2029
19. R. Karaman, A. Goldblum, E. Breuer, and H. Leader J. Chem. Soc., Perkin Trans. 1 1989 765
20. N.J. Gordon, and S.A. Evans J. Org. Chem. 58 1993 5293
21. N.J. Gordon, and S.A. Evans Phosphorus, Sulfur Silicon Relat. Elements 75 1-4 1995 47
22. E. Öhler, M. El-Badawi, and E. Zbiral Chem. Ber. 117 1984 3034
23. C. Stevens, L. De Buyck, and N. De Kimpe Tetrahedron Lett. 39 1998 8739
24. K. Afarinkia, J. Echenique, and S.C. Nyburg Tetrahedron Lett. 38 1997 1663
25. T. Okauchi, T. Yano, T. Fukomachi, J. Ichikawa, and T. Minami Tetrahedron Lett. 40 1999 5337
26. + 333.1232
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