A facile approach for the synthesis of α-halogenated alkylidenediphosphonates by reaction of alkyllithium with chlorophosphate and halogen reagent

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 179, Issue 3, 2004, Pages 449-455

  Lai, Chunbo ^a   Xi, Chanjuan ^a   Feng, Yuping ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

halogenoalkylidenediphosphonate; lithio alkylidenediphosphonate; Chlorophosphate; Halogen reagent; n alkyllithium

Indexed keywords

ALPHA BROMOBUTYLIDENEDIPHOSPHONATE; ALPHA BROMOETHYLIDENEDIPHOSPHONATE; ALPHA CHLOROBUTYLIDENEDIPHOSPHONATE; ALPHA IODOBUTYLIDENEDIPHOSPHONATE; BISPHOSPHONIC ACID DERIVATIVE; CHLORINE DERIVATIVE; HALOGEN; LITHIUM DERIVATIVE; PHOSPHATE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HALOGENATION; METHODOLOGY;

EID: 1842850533     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500490262621     Document Type: Article

References (30)

1. E. E. Aboujaoude, N. Collignon, S. Liétgé, M.-P. Teulade, and P. Savignac, Tetrahedron Lett., 26, 4435 (1985).
2. J. J. Kulagowski, R. Baker, and S. R. Fletcher, J. Chem. Soc., Chem. Commun., 22, 1649 (1991).
3. F. J. Leeper, M. Rock, and D. Appleton, J. Chem. Soc., Perkin Trans. 1, 21, 2633 (1996).
4. F. Eymery, B. Iorga, and P. Savignac, Tetrahedron, 55, 13109 (1999).
5. M. D. Francis and R. R. Martodam, Chemical, Biochemical and Medicinal Properties of the Diphosphonates in the Role of phosphonates in Living Systems, edited by R. L. Hilderbrand (CRC Press, Boca Raton, FL, 1983) vol. 55, p. 96.
6. G. M. Blackburn and M. J. Parratt, J. Chem. Soc. Perkin Trans. 1, 1417 (1986).
7. C. Li, Y. Ding, and C. Yuan, Synthesis, 854 (1991).
8. G. T. Lowen and M. R. Almond, J. Org. Chem., 59, 4548 (1994).
9. S. R. Piettre and P. Raboisson, Tetrahedron Lett., 37, 2229 (1996).
10. W. Perlikowska, M. J. Mphahlele, and T. A. Modro, J. Chem. Soc. Perkin Trans., 2, 967 (1997).
11. B. Iorga and P. Savigance, J. Organomet. Chem., 624, 203 (2001).
12. P. Cload and D. Hutchinson, Nucleic Acids Res., 11, 5621 (1983).
13. D. E. Clercq, Biochem. Pharmacol., 42, 963 (1991).
14. D. A. Nichllson and H. Vaughn, J. Org. Chem., 36, 1835 (1971).
15. D. Seyferth and R. S. Marmor, J. Organomet. Chem., 59, 237 (1973).
16. D. W. Hutchinson and D. M. Thornton, J. Organomet. Chem., 340, 93 (1988).
17. J. Vepsäläinen, H. Nupponen, E. Pohjala, M. Ahlgren, and P. Vainiotalo, J. Chem. Soc. Perkin Trans., 2, 835 (1992).
18. G. M. Blackburn, D. Brown, S. J. Martin, and M. J. Parratt, J. Chem. Soc. Perkin Trns. 1, 181 (1987).
19. X. Zhang, W. Qiu, and D. J. Burton, Tetrahedron Lett., 40, 2681 (1999).
20. G. T. Lowen and M. R. Almond, J. Org. Chem., 59, 4548 (1994).
21. W. Perlikowska, T. A. Modro, and M. J. Mphahlele, J. Chem. Soc. Perkin Trans. 2, 2611 (1996).
22. B. Iorga, F. Eymery, and P. Savignac, Tetrahedron Lett., 39, 4477 (1998).
23. O. T. Quimby, J. D. Curry, D. A. Nicholson, J. B. Prentice, and C. H. Roy, J. Organomet. Chem., 13, 199 (1968).
24. C. E. Mckenna and P. D. Shen, J. Org. Chem., 46, 4573 (1981).
25. G. M. Blackburn, D. A. England, and F. Kolkmann, J. Chem. Soc. Chem. Commun., 930 (1981).
26. C. J. Hamilton, S. M. Roberts, and A. Shipitsin, Chem. Commun., 1087 (1998).
27. M. K. Tay, E. About-Jaudet, N. Collignon, M.-P. Teulade, and P. Savignac, Synth. Commun., 18, 1349 (1988).
28. P. Savignac, M.-P. Teulade, and C. Patois, Phosphorus, Sulfur, and Silicon, 49/50, 169 (1990).
29. C. Yuan and Y. Ding, Acta Chimica Sinica, 45, 1213 (1987).
30. C. Li and C. Yuan, Tetrahedron Lett., 34, 1515 (1993).