Novel Resorcinarene Cavitand-Based CMP(O) Cation Ligands: Synthesis and Extraction Properties

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7148-7155

  Boerrigter, Harold ^a   Verboom, Willem ^b   Reinhoudt, David N ^b  

^a TNO   (Netherlands)

^b UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000539508     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9703414     Document Type: Article

References (64)

1. (a) McKay, H. A. C.; Miles, J. H.; Swanson, J. L. Science and Technology of Tributyl Phosphate; Schulz, W. W., Navratil, J. D., Eds.; CRC Press: Boca Raton, 1984; p 1.
2. (b) Miles, J. H. Science and Technology of Tributyl Phosphate; Schulz, W. W., Navratil, J. D., Eds.; CRC Press: Boca Raton, 1984; p 11.
3. For example, see: (a) Horwitz, E. P.; Kalina, D. G.; Diamond, H.; Vandegrift, G. F. Solv. Extr. Ion Exch. 1985, 3, 75. (b) Horwitz, E. P.; Schulz, W. W. New Separation Chemistry, Techniques for Radioactive Waste and other Specific Applications; Horwitz, E. P., Schulz, W. W., Eds.; Elsevier Applied Science: New York, 1991; p 21.
4. For example, see: (a) Horwitz, E. P.; Kalina, D. G.; Diamond, H.; Vandegrift, G. F. Solv. Extr. Ion Exch. 1985, 3, 75. (b) Horwitz, E. P.; Schulz, W. W. New Separation Chemistry, Techniques for Radioactive Waste and other Specific Applications; Horwitz, E. P., Schulz, W. W., Eds.; Elsevier Applied Science: New York, 1991; p 21.
5. (a) Siddall, III, T. H. J. Inorg. Nucl. Chem. 1963, 25, 883.
6. (b) Siddall, III, T. H. J. Inorg. Nucl. Chem. 1964, 26, 1991.
7. For some examples see: (a) Kalina, D. G.; Horwitz, E. P.; Kaplan, L.; Muscatello, A. C. Sep. Sci. Technol. 1981, 16, 1127. (b) Horwitz, E. P.; Kalina, D. G.; Kaplan, L.; Mason, G. W. Sep. Sci. Technol. 1982, 17, 1261. Myasoedov, B. F.; Chmutova, M. K.; Kochetkova, N. E.; Koiro, O. E.; Pribylova, G. A.; Nesterova, N. P.; Medved, T. Ya.; Kabachnik, M. I. Solv. Extr. Ion Exch. 1986, 4, 61. (d) Horwitz, E. P.; Martin, K. A.; Diamond, H.; Kaplan, L. Solv. Extr. Ion Exch. 1986, 4, 449. (e) Horwitz, E. P.; Dietz, M. L.; Fisher, D. E. Solv. Extr. Ion Exch. 1991, 9, 1.
8. For some examples see: (a) Kalina, D. G.; Horwitz, E. P.; Kaplan, L.; Muscatello, A. C. Sep. Sci. Technol. 1981, 16, 1127. (b) Horwitz, E. P.; Kalina, D. G.; Kaplan, L.; Mason, G. W. Sep. Sci. Technol. 1982, 17, 1261. Myasoedov, B. F.; Chmutova, M. K.; Kochetkova, N. E.; Koiro, O. E.; Pribylova, G. A.; Nesterova, N. P.; Medved, T. Ya.; Kabachnik, M. I. Solv. Extr. Ion Exch. 1986, 4, 61. (d) Horwitz, E. P.; Martin, K. A.; Diamond, H.; Kaplan, L. Solv. Extr. Ion Exch. 1986, 4, 449. (e) Horwitz, E. P.; Dietz, M. L.; Fisher, D. E. Solv. Extr. Ion Exch. 1991, 9, 1.
9. For some examples see: (a) Kalina, D. G.; Horwitz, E. P.; Kaplan, L.; Muscatello, A. C. Sep. Sci. Technol. 1981, 16, 1127. (b) Horwitz, E. P.; Kalina, D. G.; Kaplan, L.; Mason, G. W. Sep. Sci. Technol. 1982, 17, 1261. Myasoedov, B. F.; Chmutova, M. K.; Kochetkova, N. E.; Koiro, O. E.; Pribylova, G. A.; Nesterova, N. P.; Medved, T. Ya.; Kabachnik, M. I. Solv. Extr. Ion Exch. 1986, 4, 61. (d) Horwitz, E. P.; Martin, K. A.; Diamond, H.; Kaplan, L. Solv. Extr. Ion Exch. 1986, 4, 449. (e) Horwitz, E. P.; Dietz, M. L.; Fisher, D. E. Solv. Extr. Ion Exch. 1991, 9, 1.
10. For some examples see: (a) Kalina, D. G.; Horwitz, E. P.; Kaplan, L.; Muscatello, A. C. Sep. Sci. Technol. 1981, 16, 1127. (b) Horwitz, E. P.; Kalina, D. G.; Kaplan, L.; Mason, G. W. Sep. Sci. Technol. 1982, 17, 1261. Myasoedov, B. F.; Chmutova, M. K.; Kochetkova, N. E.; Koiro, O. E.; Pribylova, G. A.; Nesterova, N. P.; Medved, T. Ya.; Kabachnik, M. I. Solv. Extr. Ion Exch. 1986, 4, 61. (d) Horwitz, E. P.; Martin, K. A.; Diamond, H.; Kaplan, L. Solv. Extr. Ion Exch. 1986, 4, 449. (e) Horwitz, E. P.; Dietz, M. L.; Fisher, D. E. Solv. Extr. Ion Exch. 1991, 9, 1.
11. For some examples see: (a) Kalina, D. G.; Horwitz, E. P.; Kaplan, L.; Muscatello, A. C. Sep. Sci. Technol. 1981, 16, 1127. (b) Horwitz, E. P.; Kalina, D. G.; Kaplan, L.; Mason, G. W. Sep. Sci. Technol. 1982, 17, 1261. Myasoedov, B. F.; Chmutova, M. K.; Kochetkova, N. E.; Koiro, O. E.; Pribylova, G. A.; Nesterova, N. P.; Medved, T. Ya.; Kabachnik, M. I. Solv. Extr. Ion Exch. 1986, 4, 61. (d) Horwitz, E. P.; Martin, K. A.; Diamond, H.; Kaplan, L. Solv. Extr. Ion Exch. 1986, 4, 449. (e) Horwitz, E. P.; Dietz, M. L.; Fisher, D. E. Solv. Extr. Ion Exch. 1991, 9, 1.
12. Arnaud-Neu, F.; Böhmer, V.; Dozol, J.-F.; Grüttner, G.; Jakobi, R. A.; Kraft, D.; Mauprivez, O.; Rouquette, H.; Schwing-Weill, M.-J.; Simon, N.; Vogt, W. J. Chem. Soc., Perkin Trans. 2 1996, 1175.
13. Throughout this paper the trivial name cavitand will be used for the rigidified tetrameric resorcinarene frame. The official IUPAC name for the tetrakis(XX)cavitand is 7,11,15,28-tetrakis(XX)-1,21,23,25-tetrapentyl-2,20:3,19-dimetheno-1H,21H,23H, 25H-bis[1,3]dioxocino- [5,4-i:5′,4′]benzo[1,2-d:5,4-d′]bis[1,3]benzodioxocin, in which the XX refers to the substituents.
14. For reviews, see: (a) Cram, D. J.; Cram, J. M. Container Molecules and their Guests, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1994; Vol. 4. (b) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
15. For reviews, see: (a) Cram, D. J.; Cram, J. M. Container Molecules and their Guests, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1994; Vol. 4. (b) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
16. Cavitands have been used in combination with calixarenes for complexation of steroids: Higler, I.; Timmerman, P.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 5920.
17. Some examples of metal ligands based on (non-cavitand) resorcinarene derivatives have been described. (a) Octols with eight acetyl esters or amides: Fransen, J. R.; Dutton, P. J. Can. J. Chem. 1995, 73, 2217. (b) Monoanionic form of tribridged - diol resorcinarenes: Sorrell, T. N.; Pigge, F. C.; White, P. S. Inorg. Chem. 1994, 33, 632. (c) Potential ligands for silver and copper(II): Egberink, R. J. M; Cobben, P. L. H. M.; Verboom, W.; Harkema, S.; Reinhoudt, D. N. J. Incl. Phenom. 1992, 12, 151.
18. Some examples of metal ligands based on (non-cavitand) resorcinarene derivatives have been described. (a) Octols with eight acetyl esters or amides: Fransen, J. R.; Dutton, P. J. Can. J. Chem. 1995, 73, 2217. (b) Monoanionic form of tribridged - diol resorcinarenes: Sorrell, T. N.; Pigge, F. C.; White, P. S. Inorg. Chem. 1994, 33, 632. (c) Potential ligands for silver and copper(II): Egberink, R. J. M; Cobben, P. L. H. M.; Verboom, W.; Harkema, S.; Reinhoudt, D. N. J. Incl. Phenom. 1992, 12, 151.
19. Some examples of metal ligands based on (non-cavitand) resorcinarene derivatives have been described. (a) Octols with eight acetyl esters or amides: Fransen, J. R.; Dutton, P. J. Can. J. Chem. 1995, 73, 2217. (b) Monoanionic form of tribridged - diol resorcinarenes: Sorrell, T. N.; Pigge, F. C.; White, P. S. Inorg. Chem. 1994, 33, 632. (c) Potential ligands for silver and copper(II): Egberink, R. J. M; Cobben, P. L. H. M.; Verboom, W.; Harkema, S.; Reinhoudt, D. N. J. Incl. Phenom. 1992, 12, 151.
20. (a) Van Wageningen, A. M. A.; Boerrigter, H.; Snip, E.; Verboom, W.; Reinhoudt, D. N. Liebigs Ann./Recueil 1997, in press.
21. (b) Kim, K.; Paek, K. Bull. Korean Chem. Soc. 1993, 14, 659.
22. Boerrigter, H.; Konings, R. J. M.; Cordfunke, E. H. P.; Verboom, W.; Reinhoudt, D. N. GLOBAL'95, International Conference on Evaluation of Emerging Nuclear Fuel Cycle Systems; 1995, Vol. 2, p 1252.
23. (a) Seaborg, G. T. Radiochim. Acta 1993, 61, 115.
24. (b) Choppin, G. R.; Rizkalla, E. N. Handbook of the Physics and Chemistry of Rare Earths; Gschneider, K. A., Jr., Eyring, L., Choppin, G. R., Lander, G. H., Eds.; Elsevier Science: Amsterdam, 1994; Vol. 18, p 559.
25. Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305.
26. 1H NMR spectrum, some impurities were present that interfered with subsequent reactions. After chromatography of the crude product over 2 cm of silica, cavitand 2 was obtained in pure form.
27. (a) H. Boerrigter, Unpublished results,
28. (b) Timmerman, P.; Boerrigter, H.; Verboom, W.; Van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Incl. Phenom. 1994, 19, 167.
29. (c) Bryant, J. A.; Blanda, M. T.; Vicenti, M.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2167.
30. (d) Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 2229.
31. Sorrell, T. N.; Pigge, F. C. J. Org. Chem. 1993, 58, 784.
32. The conditions reported by Sorrell and Pigge were (in our hands) not successful.
33. Boerrigter, H.; Verboom, W.; Van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron Lett. 1996, 37, 5167.
34. Landini, D.; Rolla, F. Synthesis 1976, 389.
35. Gatrone, R. C.; Kaplan, L.; Horwitz, E. P. Solv. Extr. Ion Exch. 1987, 5, 1075.
36. For a review see: Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. (Washington, D.C.) 1981, 81, 415.
37. In general, the purification of reaction products from Arbusov reactions is difficult, due to the high boiling points of the Arbusov reagents and the instability of the products on different column materials (e.g. silica and aluminum oxide). Recrystallization or precipitation of the products are useful in some cases, but does often not allow satisfying results. Purification with Sephadex LH-20 column chromatography is an excellent method in these cases, as the Arbusov reagents are generally much smaller (have a smaller molecular volume) than the macrocyclic derivatives. Furthermore, no product is lost due to decomposition on, or interactions with, the column material.
38. (a) Mohapatra, P. K.; Manchanda, V. K. Radiochim. Acta 1991, 55, 193.
39. (b) Manchanda, V. K.; Mohapatra, P. K. Radiochim. Acta 1995, 69, 81.
40. Takeda, Y. Top. Curr. Chem. 1984, 121, 1.
41. Horwitz, E. P.; Dietz, M. L.; Fisher, D. E. Solv. Extr. Ion Exch. 1991, 9, 1.
42. The values presented in Table 2 have been rounded off; however, the calculations were performed with the exact values.
43. Horwitz, E. P.; Diamond, H.; Kalina, D. G. Plutonium Chemistry; ACS Symposium Series No. 216; Carnall, W. C., Choppin, G., Eds.; American Chemical Society: Washington DC, 1983; p 433.
44. Ozawa, M.; Nemeto, S.; Togashi, A.; Kawata, T.; Onishi, K. Solv. Extr. Ion Exch. 1992, 10, 829.
45. Baker, J. D.; Mincher, B. J.; Meikrantz, D. H.; Berreth, J. R. Solv. Extr. Ion Exch. 1988, 6, 1049.
46. Reference 4d, and references cited therein.
47. o,i cannot be made.
48. The data points of the extraction of thorium (and to lesser extent europium) with tetra-CMPO calix[4]arene derivatives in the same concentration range in the study of Böhmer et al. can also be interpreted as a curved trend. However, the authors suggested a linear correlation.
49. 3) in a standard extraction experiment.
50. These values are in good agreement with IR data for CMPO derivatives: (a) Martin, K. A.; Horwitz, E. P.; Ferraro, J. R. Solv. Extr. Ion Exch. 1986, 4, 1149. (b) ref. 4b.
51. These values are in good agreement with IR data for CMPO derivatives: (a) Martin, K. A.; Horwitz, E. P.; Ferraro, J. R. Solv. Extr. Ion Exch. 1986, 4, 1149. (b) ref. 4b.
52. -3 M, pH 3.0), bidentate behavior was also found. See: Muscatello, A. C.; Horwitz, E. P.; Kalina, D. G.; Kaplan, L. Sep. Sci. Technol. 1982, 17, 859.
53. Cook, A. G.; Mason, G. W. J. Inorg. Nucl. Chem. 1973, 35, 2093.
54. (a) Timko, J. M.; Moore, S. S.; Walba, D. M.; Hiberty P. C.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 4207.
55. (b) Newcomb, M.; Timko, J. M.; Walba, D. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6392.
56. (c) Moore, S. S.; Tarnowski, T. L.; Newcomb, M, Cram, D. J. J. Am Chem. Soc. 1977, 99, 6398.
57. (d) Koening, K. E.; Lein, G. M.; Stuckler, P., Kaneda, T.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3553.
58. o (half-protonation) values are 2.13 and 1.62, respectively: The Chemistry of Amides; Zabicky, J., Patai, S., Eds.; John Wiley & Sons: London, 1970; p 210.
59. (40) Handbook of Chemistry and Physics, 73rd ed.; Lide, D. R., Ed.: CRC Press: London, 1992-1993, p 8-40.
60. (a) Concerning lanthanides: Ohyoshi, A.; Ohyoshi, E.; Ono, H.; Yamakawa, S. J. Inorg. Nucl. Chem. 1972, 34, 1955.
61. II(OH): The Hydrolysis of Cations, Baes, C. F., Jr., Mesmer, R. E., Eds.; John Wiley & Sons: New York, 1976; pp 410-411.
62. Especially for Fe(III), it is known that establishment of the extraction equilibrium with CMP(O) derivatives requires longer mixing times due to the slow kinetics (see ref 4a).
63. (a) Flick, E. W. (Ed.) Industrial Solvents Handbook, 3rd ed.; Noyes Data Corporation: Park Ridge, 1985; pp 118, 151.
64. (b) Stephen, H.; Stephen, T. (Eds.) Solubilities of Inorganic and Organic Compounds; Pergamon Press: London, 1963; Vol. 1, Part 1, p 371.