Cobalt bis(dicarbollides)(1-) Covalently attached to the calix[4]arene platform: The first combination of organic bowl-shaped matrices and inorganic metallaborane cluster anions

European Journal of Organic Chemistry

Volumn , Issue 10, 2005, Pages 2022-2039

  Grüner, Bohumír ^a   Mikulášek, Libor ^a   Báča, Jiří ^a   Císařová, Ivana ^b   Böhmer, Volker ^c   Danila, Crenguta ^c   Reinoso García, Marta M ^d   Verboom, Willem ^d   Reinhoudt, David N ^d   Casnati, Alessandro ^e   Ungaro, Rocco ^e  

^a INSTITUTE OF INORGANIC CHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

^d UNIVERSITY OF TWENTE   (Netherlands)

^e UNIVERSITY OF PARMA   (Italy)

Author keywords

Calixarenes; Carboranes; Dicarbollides; Metallacarboranes; Resorcarene cavitands

Indexed keywords

EID: 19844367170     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400811     Document Type: Article

References (86)

1. a) Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, Boston, London, 2001;
2. b) C. D. Gutsche, Calixarenes Revisited (Ed.: J. F. Stoddard), The Royal Society of Chemistry, Cambridge, 1998.
3. V. Böhmer, Angew. Chem. 1995, 107, 785-818;
4. Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745.
5. W. Verboom, Cavitands, chapter 9, in Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, Boston, London, 2001, pp. 181-198.
6. P. Timmerman, W. Verboom, D. N. Reinhoudt, Tetrahedron 1996, 52, 2663-2704.
7. A. Thorndorf, A. Shivanyuk, V. Böhmer, Chemical Modification of Calix [4] arenes and Resorcarenes, chapter 2, in Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, Boston, London, 2001, pp. 26-54.
8. For recent examples of water-soluble Calixarenes and cavitands see, for example: a) O. Middel, W. Verboom, D. N. Reinhoudt, Eur. J. Org. Chem. 2002, 2587-2597;
9. b) M. Makha, I. R. McKinnon, C. L. Raston, J. Chem. Soc., Perkin Trans. 2 2002, 1801-1806;
10. c) A. Casnati, D. Sciotto, G. Arena, Water-Soluble Calixarenes, chapter 24, in Calixarenes 2001 (Eds.:Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht-Boston-London, 2001, pp. 440-457.
11. V. Böhmer, M. A. McKervey, Chem. Unserer Zeit 1991, 25, 195-207.
12. F. Sansone, M. Segura, R. Ungaro, Calixarenes in Bioorganic and Biomimetic Chemistry, chapter 2, in Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, Boston, London, 2001.
13. a) A. Casnati, F. Sansone, R. Ungaro, Acc. Chem. Res. 2003, 36, 246-254;
14. b) D. A. Fulton, J. F. Stoddart, Bioconjugate Chem. 2001, 12, 655-672;
15. c) T. Nakai, T. Kanamori, S. Sando, Y. Aoyama, J. Am. Chem. Soc. 2003, 125, 8465-8475;
16. Y. Aoyama, Chem. Eur. J. 2004, 10, 588-593.
17. A. R. Mezo, J. C. Sherman, J. Am. Chem. Soc. 1999, 121, 8983-8994.
18. a) Y. Hamuro, M. C. Calama, H. S. Park, A. D. Hamilton, Angew. Chem. 1997, 109, 2797-2800;
19. Angew. Chem. Int. Ed. Engl. 1997, 36, 2680-2683;
20. b) H. S. Park, Q. Lin, A. D. Hamilton, J. Am. Chem. Soc. 1999, 121, 8-13.
21. a) L. Baldini, C. Bracchini, R. Cacciapaglia, A. Casnati, L. Mandolini, R. Ungaro, Chem. Eur. J. 2000, 6, 1322-1330;
22. b) P. Molenveld, J. F. J. Engbersen, H. Kooijman, A. L. Spek, D. N. Reinhoudt, J. Am. Chem. Soc. 1998, 120, 6726-6737;
23. c) Y. Rondelez, G. Bertho, O. Reinaud, Angew. Chem. 2002, 114, 1086-1088;
24. Angew. Chem. Int. Ed. 2002, 41, 1044-1045.
25. R. Roy, J. M. Kim, Angew. Chem. 1999, 111, 380-384;
26. Angew. Chem. Int. Ed. 1999, 38, 369-372.
27. G. Moschetto, R. Lauceri, F. G. Gulino, D. Sciotto, R. Purrello, J. Am. Chem. Soc. 2002, 124, 14536-14537.
28. M. O. Vysotsky, V. Böhmer, F. Würthner, C. C. You, K. Rissanen, Org. Lett. 2002, 4, 2901-2904.
29. For recent reviews and examples see: a) D. M. Rudkevich, Self-Assembly in Solution, Chapter 8, in Calixarenes 2001 (Eds.: Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens), Kluwer Academic Publishers, Dordrecht, Boston, London, 2001, pp. 155-181;
30. b) V. Böhmer, M. O. Vysotsky, Aust. J. Chem. 2001, 54, 671-677;
31. c) F. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Angew. Chem. 2002, 114, 1556-1578;
32. Angew. Chem. Int. Ed. 2002, 41, 1488-1508;
33. d) T. Amaya, J. Rebek, J. Am. Chem. Soc. 2004, 126, 6216-6217;
34. e) F. Sansone, L. Baldini, A. Casnati, E. Chierici, G. Faimani, F. Ugozzoli, R. Ungaro, J. Am. Chem. Soc. 2004, 126, 6204-6205;
35. f) F. Corbellini, L. Di Costanzo, M. Crego-Calama, S. Geremia, D. N. Reinhoudt, J. Am. Chem. Soc. 2003, 125, 9946-9947.
36. a) R. Ungaro, A. Casnati, F. Ugozzoli, A. Pochini, J. F. Dozol, C. Hill, H. Rouquette, Angew. Chem. 1994, 106, 1551-1553
37. Angew. Chem. Int. Ed. Engl. 1994, 33, 1506-1509;
38. b) A. Casnati, A. Pochini, R. Ungaro, F. Ugozzoli, F. Arnaud, S. Fanni, M. J. Schwing, R. J. M. Egberink, F. De Jong, D. N. Reinhoudt, J. Am. Chem. Soc. 1995, 117, 2767-2777.
39. a) A. Casnati, L. Baldini, N. Pelizzi, K. Rissanen, F. Ugozzoli, R. Ungaro, J. Chem. Soc., Dalton Trans. 2000, 3411-3415;
40. b) A. Casnati, S. Barboso, H. Rouquette, M. J. Schwing-Weill, F. Arnaud-Neu, J. F. Dozol, R. Ungaro, J. Am. Chem. Soc. 2001, 123, 12182-12190.
41. a) L. H. Delmau, N. Simon, M. J. Schwing-Weill, F. Arnaud-Neu, J. F. Dozol, S. Eymard, B. Tournois, V. Böhmer, C. Grüttner, C. Musigmann, A. Tunayar, Chem. Commun. 1998, 1627-1628;
42. b) S. Barboso, A. G. Carrera, S. E. Matthews, F. Arnaud-Neu, V. Böhmer, J. F. Dozol, H. Rouquette, M. J. Schwing-Weill, J. Chem. Soc., Perkin Trans. 2 1999, 719-723;
43. c) B. Lambert, V. Jacques, A. Shivanyuk, S. E. Matthews, A. Tunayar, M. Baaden, G. Wipff, V. Böhmer, J. F. Desreux, Inorg. Chem. 2000, 39, 2033-2041;
44. d) C. Schmidt, M. Saadioui, V. Böhmer, V. Host, M. R. Spirlet, J. F. Desreux, F. Brisach, F. Arnaud-Neu, J. F. Dozol, Org. Biomol. Chem. 2003, 1, 4089-4096.
45. F. Arnaud-Neu, S. Barboso, A. Casnati, A. Pinalli, M. J. Schwing-Weill, R. Ungaro, New J. Chem. 2000, 24, 967-972.
46. a) H. Boerrigter, W. Verboom, D. N. Reinhoudt, Liebigs Ann./ Recl. 1997, 2247-2254;
47. b) H. Boerrigter, T. Tomasberger, W. Verboom, D. N. Reinhoudt, Eur. J. Org. Chem. 1999, 665-674;
48. c) H. Boerrigter, W. Verboom, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 7148-7155.
49. M. F. Hawthorne, T. D. Andrews, J. Chem. Soc., Chem. Commun. 1965, 443-444.
50. I. B. Sivaev, V. I. Bregadze, Collect. Czech. Chem. Commun. 1999, 64, 783-805.
51. a) S. H. Strauss, Chem. Rev. 1993, 93, 927-942;
52. b) C. A. Reed, Acc. Chem. Res. 1998, 31, 133-139.
53. J. Plešek, Chem. Rev. 1992, 92, 269-278.
54. M. F. Hawthorne, A. Maderna, Chem. Rev. 1999, 99, 3421-3434.
55. J. Rais, B. Grüner, Extraction with Metal bis(dicarbollide) Anions; Metal bis(dicarbollide) Extradants and their Applications in Separation Chemistry, in Ion Exchange, Solvent extraction, vol. 17 (Eds.: Y. Marcus, A. K. SenGupta), Marcel Dekker, New York, 2004, pp. 243-334.
56. a) R. S. Herbst, J. D. Law, T. A. Todd, V. N. Romanovskiy, V. A. Babain, V. M. Esimantovskiy, I. V. Smirnov, B. N. Zaitsev, Solvent Extr. Ion Exch. 2002, 20, 429-445;
57. b) R. S. Herbst, J. D. Law, T. A. Todd, V. N. Romanovskii, V. A. Babain, V. M. Esimantovski, B. N. Zaitsev, I. V. Smirnov, Sep. Sci. Technol. 2002, 37, 1807-1831;
58. c) V. N. Romanovskiy, I. V. Smirnov, V. A. Babain, T. A. Todd, R. S. Herbst, J. D. Law, K. N. Brewer, Solvent Extr. Ion Exch. 2001, 19, 1-21;
59. d) J. D. Law, R. S. Herbst, T. A. Todd, V. N. Romanovskiy, V. A. Babain, V. M. Esimantovskiy, I. V. Smirnov, B. N. Zaitsev, Solvent Extr. Ion Exch. 2001, 19, 23-36.
60. B. Grüner, J. Plešek, J. Báča, I. Cisařová, J. F. Dozol, H. Rouquette, C. Viňas, P. Selucký, J. Rais, New J. Chem. 2002, 26, 1519-1527.
61. J. Plešek, B. Grüner, I. Císařová, J. Báča, P. Selucký, J. Rais, J. Organomet. Chem. 2002, 657, 59-70.
62. a) S. Shinkai, T. Arimura, K. Araki, H. Kawabata, H. Satoh, T. Tsubaki, O. Manabe, J. Sunamoto, J. Chem. Soc., Perkin Trans. 1 1989, 2039-2045;
63. b) S. Shinkai, H. Kawabata, T. Arimura, T. Matsuda, H. Satoh, O. Manabe, J. Chem. Soc., Perkin Trans. 1 1989, 1073-1074.
64. A. Arduini, A. Pochini, S. Reverberi, R. Ungaro, J. Chem. Soc., Chem. Commun. 1984, 981-982.
65. a) P. D. Beer, A. D. Keefe, M. G. B. Drew, J. Organomet. Chem. 1989, 378, 437-447;
66. b) P. D. Beer, A. D. Keefe, V. Böhmer, H. Goldmann, W. Vogt, S. Lecocq, M. Perrin, J. Organomet. Chem. 1991, 421, 265-273.
67. a) M. J. Hardie, C. L. Raston, Eur. J. Inorg. Chem. 1999, 195-200;
68. b) M. J. Hardie, C. L. Raston, Chem. Commun. 1999, 1153-1163.
69. C. L. Raston, G. W. V. Cave, Chem. Eur. J. 2004, 10, 279-282.
70. J. Plešek, S. Heřmánek, A. Franken, I. Císařová, C. Nachtigal, Collect. Czech. Chem. Commun. 1997, 64, 47-56.
71. J. Plešek, B. Grüner, S. Heřmánek, J. Báča, V. Mareček, J. Janchenová, A. Lhotský, K. Holub, P. Selucký, J. Rais, I. Císařová, J. Časlavský, Polyhedron 2002, 21, 975-986.
72. a) B. Grüner, J. Plešek, J. Báča, J. F. Dozol, V. Lamare, I. Cisařová, M. Bělohradský, J. Čáslavský, New J. Chem. 2002, 26, 867-875;
73. b) I. B. Sivaev, Z. A. Starikova, S. Sjöberg, V. I. Bregadze, J. Organomet. Chem. 2002, 649, 1-8.
74. F. Sansone, S. Barboso, A. Casnati, M. Fabbi, A. Pochini, F. Ugozzoli, R. Ungaro, Eur. J. Org. Chem. 1998, 897-905.
75. J. Plešek, S. Heřmánek, L. J. Todd, W. F. Wright, Collect. Czech. Chem. Commun. 1976, 41, 3509-3515.
76. V. Böhmer, Calixarenes, in The Chemistry of Phenols, Wiley, Chichester, 2003.
77. J. M. Harrowfield, M.I. Ogden, W. R. Richmond, A. H. White, J. Chem. Soc., Chem. Commun. 1991, 1159-1161.
78. a) R. J. Bernardino, B. J. C. Cabral, Supramol. Chem. 2002, 14, 57-66;
79. b) R. Dubberley, A. J. Blake, P. Mountford, Dalton Trans. 2003, 2418-2427.
80. D. F. Shriver, M. A. Drezdon, Manipulation of Air Sensitive Compounds, Series, Wiley, New York, 1986.
81. a) V. Böhmer, K. Jung, M. Schön, A. Wolff, J. Org. Chem. 1992, 57, 790-792;
82. b) C. D. Gutsche, K. A. See, J. Org. Chem. 1992, 57, 4527-4539.
83. a) Z. Plzák, J. Plešek, B. Štíbr, J. Chromatogr. 1981, 212, 283-293;
84. b) B. Grüner, Z. Plzák, J. Chromatogr. A 1997, 789, 497-517.
85. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435-443.
86. SHELXL97, Program for the Solution of Crystal Structures, University of Göttingen, Göttingen (Germany), 1997.