Cyclodextrin phosphanes as first and second coordination sphere cavitands

Chemistry - A European Journal

Volumn 9, Issue 13, 2003, Pages 3091-3105

  Engeldinger, Eric ^a   Armspach, Dominique ^a   Matt, Dominique ^a   Jones, Peter G ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Cavitands; Cyclodextrins; Inclusion compounds; Metallocavitands; Phosphanes

Indexed keywords

ACETONITRILE; DISSOCIATION; ELECTRONS; TRANSITION METALS;

LIGANDS;

COMPLEXATION;

ACETONITRILE; ALPHA CYCLODEXTRIN; BENZONITRILE; CYCLODEXTRIN DERIVATIVE; LIGAND; SILVER DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

CYCLODEXTRINS; ETHERS, CYCLIC; MOLECULAR STRUCTURE; PHOSPHINES; RESORCINOLS;

EID: 0042808679     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304806     Document Type: Article

References (77)

1. Cyclodextrins: Comprehensive Supramolecular Chemistry, Vol. 3 (Eds.: J. L. Altwood, J. E. D. Davies, D. D. Macinol, F. Vögtle, J.-M. Lehn), Pergamon, Oxford, 1996.
2. Modified Cyclodextrins (Eds.: C. J. Easton, S. F. Lincoln), Imperial College Press, London, 1999.
3. S. Cherkaoui, S. Rudaz, E. Varesio, J.-L. Veuthey, Electrophoresis 2001, 22, 3308.
4. G. Gübitz, M. G. Schmid, Biopharm. Drug Dispos. 2001, 22, 291.
5. M. Wedig, S. Laug, T. Christians, M. Thunhorst, U. Holzgrabe, J. Pharm. Biomed. Anal. 2002, 27, 531.
6. M. R. Craig, M. G. Hutchings, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2001, 113, 1105; Angew. Chem. Int. Ed. 2001, 40, 1071.
7. M. R. Craig, M. G. Hutchings, T. D. W. Claridge, H. L. Anderson, Angew. Chem. 2001, 113, 1105; Angew. Chem. Int. Ed. 2001, 40, 1071.
8. M. Skiba, D. Duchêne, F. Puisieux, D. Wouessidjewe, Int. J. Pharm. 1996, 129, 113.
9. M. Skiba, F. Nemati, F. Puisieux, D. Duchêne, D. Wouessidjewe, Int. J. Pharm. 1996, 145, 241.
10. V. J. Stella, V. M. Rao, E. A. Zannou, V. Zia, Adv. Drug. Delivery Rev. 1999, 36, 3.
11. F. Hirayama, K. Uekama, Adv. Drug. Delivery Rev. 1999, 36, 125.
12. I. Tabushi, Acc. Chem. Res. 1982, 15, 66.
13. E. U. Akkaya, A. W. Czarnik, J. Am. Chem. Soc. 1988, 110, 8553.
14. R. Breslow, G. Zhang, J. Am. Chem. Soc. 1992, 114, 5882.
15. Y. Murakami, J.-I. Kikichi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721.
16. R. Breslow, S. Dong, Chem. Rev. 1998, 98, 1997.
17. E. Rizzarelli, G. Vecchio, Coord. Chem. Rev. 1999, 188, 343.
18. J. Emert, R. Breslow, J. Am. Chem. Soc. 1975, 97, 670.
19. I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855.
20. M. Sawamura, K. Kitayama, Y. Ito, Tetrahedron: Asymmetry 1993, 4, 1829.
21. M. T. Reetz, J. Rudolph, Tetrahedron: Asymmetry 1993, 4, 2405.
22. M. T. Reetz, Catal. Today 1998, 42, 399.
23. D. Armspach, D. Matt, Chem. Commun. 1999, 1073.
24. M. T. Reetz, C. Frömbgen, Synthesis 1999, 1555.
25. D. Armspach, D. Matt, A. Harriman, Eur. J. Inorg. Chem. 2000, 1147.
26. D. Armspach, D. Matt, Inorg. Chem. 2001, 40, 3505.
27. D. Armspach, D. Matt, N. Kyritsakas, Polyhedron 2001, 20, 663.
28. M. T. Reetz, J. Rudolph, R. Goddard, Can. J. Chem. 2001, 79, 1806.
29. C. Yang, Y. K. Cheung, J. Yao, Y. T. Wong, G. Jia, Organometallics 2001, 20, 424.
30. C. Yang, Y. T. Wong, Z. Li, J. J. Krepinsky, G. Jia, Organometallics 2001, 20, 5220.
31. E. Engeldinger, D. Armspach, D. Matt, L. Toupet, M. Wesolek, C. R. Chimie 2002, 5, 359.
32. Y. T. Wong, C. Yang, K.-C. Ying, G. Jia, Organometallics 2002, 21, 1782.
33. M. T. Reetz, I. D. Kostas, S. R. Waldvogel, Inorg. Chem. Commun. 2002, 5, 252.
34. M. T. Reetz, S. R. Waldvogel, Angew. Chem. 1997, 109, 870; Angew. Chem. Int. Ed. 1997, 36, 865.
35. M. T. Reetz, S. R. Waldvogel, Angew. Chem. 1997, 109, 870; Angew. Chem. Int. Ed. 1997, 36, 865.
36. C. Wieser-Jeunesse, D. Matt, A. De Cian, Angew. Chem. 1998, 110, 3027; Angew. Chem. Int. Ed. 1998, 37, 2861.
37. C. Wieser-Jeunesse, D. Matt, A. De Cian, Angew. Chem. 1998, 110, 3027; Angew. Chem. Int. Ed. 1998, 37, 2861.
38. B. R. Cameron, S. J. Loeb, G. P. A. Yap, Inorg. Chem. 1997, 36, 5498-5504.
39. M. Lejeune, C. Jeunesse, D. Matt, N. Kyritsakas, R. Welter, J.-P. Kintzinger, J. Chem. Soc. Dalton Trans. 2002, 1642.
40. S. Blanchard, L. Le Clainche, M.-N. Rager, B. Chansou, J.-P. Tuchagues, A. F. Duprat, Y. Le Mest, O. Reinaud, Angew. Chem. 1998, 110, 2861; Angew. Chem. Int. Ed. 1998, 37, 2732.
41. S. Blanchard, L. Le Clainche, M.-N. Rager, B. Chansou, J.-P. Tuchagues, A. F. Duprat, Y. Le Mest, O. Reinaud, Angew. Chem. 1998, 110, 2861; Angew. Chem. Int. Ed. 1998, 37, 2732.
42. L. Le Clainche, Y. Rondelez, O. Sénèque, S. Blanchard, M. Campion, M. Giorgi, A. F. Duprat, Y. Le Mest, O. Reinaud, C. R. Acad. Sci. Ser. IIc 2000, 3, 811.
43. Y. Rondelez, O. Sénèque, M.-N. Rager, A. Duprat, O. Reinaud, Chem. Eur. J. 2000, 6, 4218.
44. O. Sénèque, M.-N. Rager, M. Giorgi, O. Reinaud, J. Am. Chem. Soc. 2000, 122, 6183.
45. O. Sénèque, Y. Rondelez, L. Le Clainche, C. Inisan, M.-N. Rager, M. Giorgi, O. Reinaud, Eur. J. Inorg. Chem. 2001, 2597.
46. O. Sénèque, M. Giorgi, O. Reinaud, Chem. Commun. 2001, 984.
47. O. Sénèque, M.-N. Rager, M. Giorgi, O. Reinaud, J. Am. Chem. Soc. 2001, 123, 8442.
48. Y. Rondelez, M.-N. Rager, A. Duprat, O. Reinaud, J. Am. Chem. Soc. 2002, 124, 1334.
49. C. Gibson, J. Rebek, Organic Lett. 2002, 4, 1887.
50. E. Engeldinger, D. Armspach, D. Matt, Angew. Chem. 2001, 113, 2594; Angew. Chem. Int. Ed. 2001, 40, 2526.
51. E. Engeldinger, D. Armspach, D. Matt, Angew. Chem. 2001, 113, 2594; Angew. Chem. Int. Ed. 2001, 40, 2526.
52. E. Engeldinger, D. Armspach, D. Matt, P. G. Jones, R. Welter, Angew. Chem. 2002, 114, 2705; Angew. Chem. Int. Ed. 2002, 41, 2593.
53. E. Engeldinger, D. Armspach, D. Matt, P. G. Jones, R. Welter, Angew. Chem. 2002, 114, 2705; Angew. Chem. Int. Ed. 2002, 41, 2593.
54. Some insoluble material, presumably of oligomeric nature, was also formed during this synthesis of 2a, 2b, 3a and 3b. However, this is not the case for complexes 4a, 4b, 5a, 5b and 7a, which were obtained from starting complexes containing very good leaving groups.
55. 13C NMR of Transition Metal Phosphine Complexes (Eds.: P. Drehl, E. Fluck, R. Kosfeld), Springer, Berlin, 1979.
56. C. A. Bessel, P. Aggarwal, A. C. Marschilok, K. J. Takeuchi, Chem. Rev. 2001, 101, 1031.
57. L. Manojlovic-Muir, K. W. Muir, M. C. Grossel, K. A. Asker, K. R. Seddon, Transition Met. Chem. 1987, 12, 182.
58. A. P. H. J. Schenning, J.-D. Arndt, M. Ito, A. Stoddart, M. Schreiber, P. Siemsen, R. E. Martin, C. Boudon, J.-P. Gisselbrecht, M. Gross, V. Gramlich, F. Diederich, Helv. Chim. Acta 2001, 84, 296.
59. A. M. Freeman, D. A. Young, Inorg. Chem. 1986, 25, 1556-1560.
60. R. Taylor, O. Kennard, J. Am. Chem. Soc. 1982, 104, 5063-5070.
61. - ion and a MeO-3 oxygen atom. Similar noncovalent aggregates are known to withstand the conditions used for this ESI-MS experiment.
62. Coordinated MeCN molecules could not be differentiated from uncoordinated ones.
63. This includes H-1, H-2, H-4, H-6, MeO-3 and MeO-6 protons. Molecular models show that coordinated MeCN molecules not entrapped inside the cavity would result in strong steric interactions with some of the MeO-6 and H-6 protons.
64. Because of the C2 symmetry, the B and C glucose units are respectively equivalent to the E and F moities.
65. -1].
66. 2 and hence the corresponding activation barriers could not be determined accurately.
67. K. R. Dunbar, J.-S. Sun, S. C. Haefner, J. H. Matonic, Organometallics 1994, 13, 2713.
68. R. E. Bachman, D. F. Andretta, Inorg. Chem. 1998, 37, 5657.
69. M. Camalli, F. Caruso, S. Chaloupka, P. N. Kapoor, P. S. Pregosin, L. M. Venanzi, Helv. Chim. Acta 1984, 67, 1603.
70. D. K. Johnson, P. S. Pregosin, L. M. Venanzi, Helv. Chim. Acta 1976, 59, 2691.
71. Unlike the MeO-2 groups, the MeO-3 protons are known to point towards the cavity interior.
72. The 2D ROESY spectrum shows NOEs between the coordinated acetonitrile protons and three H-5 (A,C,E) protons, three H-3 (B,C,D) protons as well as some MeO-3 groups. No correlation with the aromatic protons, nor with the primary OMe groups were detected.
73. A. M. A. van Wageningen, P. Timmerman, J. P. M. van Duynhoven, W. Verboom, F. C. J. M. van Veggel, D. N. Reinhoudt, Chem. Eur. J. 1997, 3, 639.
74. V. D. Bianco, S. Doronzo, Inorg. Synthesis 1976, 16, 161.
75. F. R. Hartley, The Chemistry of Platinum and Palladium, Wiley, New York, 1973.
76. R. E. Rülke, J. M. Ernsting, A. L. Spek, Inorg. Chem. 1993, 32, 5769.
77. G. M. Sheldrick, SHELX-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.