Design of neutral, mono- or di-cationic water-soluble trihydrazidophosphoradamantanes

Tetrahedron Letters

Volumn 47, Issue 16, 2006, Pages 2687-2690

  Zabłocka, Maria ^a   Duhayon, Carine ^b  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; CATION; TRIHYDRAZIDOPHOSPHORADAMANTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DRUG DESIGN;

EID: 33644969794     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.096     Document Type: Article

References (26)

1. For a recent review, see: N. Pinault, and D.W. Bruce Coord. Chem. Rev. 241 2003 1
2. J.G. Verkade Coord. Chem. Rev. 137 1994 233
3. D.J. Daigle, A.B. Pepperman, and S.L. Vail J. Heterocycl. Chem. 11 1974 407
4. For a recent review, see: A.D. Phillips, L. Gonsalvi, A. Romerosa, F. Vizza, and M. Peruzzini Coord. Chem. Rev. 248 2004 955
5. See for example: C.S. Allardyce, P.J. Dyson, D.J. Ellis, and S.L. Heath Chem. Commun. 2001 1396
6. Z. Assefa, B.G. McBurnett, R.J. Staples, J.P. Fackler, B. Assamann, K. Angermaier, and H. Schmidbaur Inorg. Chem. 34 1995 75
7. Z. Assefa, M.A. Omary, B.G. McBurnett, A.A. Mohamed, H.H. Patterson, R.J. Staples, and J.P. Fackler Inorg. Chem. 41 2002 6274
8. J.P. Majoral, R. Kraemer, J. Navech, and F. Mathis Tetrahedron 32 1976 2633
9. J. Navech, R. Kraemer, and J.P. Majoral Tetrahedron Lett. 21 1980 1449
10. J.P. Majoral Synthesis 8 1978 557
11. J. Jaud, M. Benhamou, J.P. Majoral, and J. Navech Z. Kristallogr. 160 1982 69
12. R. Romeo, L.A. Wozniak, and C. Chatgilialoglu Tetrahedron Lett. 41 2000 9899
13. J. Omelańczuk, and M. Mikołajczyk J. Am. Chem. Soc. 101 1979 7292
14. 3: C, 26.23; H, 4.95; N, 22.94. Found: C, 26.16; H, 4.87; N, 22.90.
15. 3: C, 24.12; H, 4.55; N, 21.10. Found: C, 24.07; H, 4.48; N, 21.19.
16. 3: C, 25.13; H, 4.75; N, 21.98. Found: C, 25.16; H, 4.67; N, 21.82.
17. Crystallographic data (excluding structure factors) for the structure in this letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC294642.
18. 2S: C, 46.07; H, 4.83; N, 18.80. Found: C, 46.12; H, 4.79; N, 18.72.
19. C. Galliot, C. Larre, A.M. Caminade, and J.P. Majoral Science 277 1997 1981
20. C. Larre, A.M. Caminade, and J.P. Majoral Angew. Chem., Int. Ed. 36 1997 596
21. A.N. Johnson Ylides and Imines of Phosphorus 1993 John Wiley Sons 452
22. Schanen, V.; Cristau, H. J.; Taillefer, M. WO Patent, 2002, 092226. Chem. Abstr. 137, 386310.
23. A. Pleschke, A. Marhold, M. Schneider, A. Kolomeitsev, and G.V. Röschenthaler J. Fluorine Chem. 125 2004 1031
24. 2Br: C, 51.62; H, 5.42; N, 17.56. Found: C, 51.58; H, 5.38; N, 17.60.
25. 3: C, 43.22; H, 4.60; N, 13.57. Found: C, 43.14; H, 4.52; N, 13.48.
26. No cleavage of the P-N bond was detected in all these experiments confirming the rigidity brought about by the adamantane skeleton.