Synthesis of neutral, water-soluble calix[4]arenes

Synthesis

Volumn , Issue 6, 1997, Pages 643-648

  Grote Gansey, Marcel H B ^a   Steemers, Frank J ^a   Verboom, Willem ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

Neutral water soluble calix 4 arenes one step (de)protection

Indexed keywords

AMINE; CALIXARENE; WATER;

ARTICLE; CHEMICAL REACTION; HYDROPHOBICITY; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SOLUBILITY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0344484991     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-4506     Document Type: Article

References (47)

1. (a) Gutsche, C. D. Calixarenes, Monographs in Supramolecular Chemistry, Vol. 1.; Stoddart, J. F., Ed.: The Royal Society of Chemistry: Cambridge, 1989.
2. (b) Calixarenes, A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.: Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
3. (c) Böhmer, V. Angew. Chem. 1995, 107, 785; Angew. Chem., Intl. Ed. Engl. 1995, 34, 713.
4. (c) Böhmer, V. Angew. Chem. 1995, 107, 785; Angew. Chem., Intl. Ed. Engl. 1995, 34, 713.
5. Van Loon, J.-D.; Verboom, W.; Reinhoudt, D. N. Org. Prep. Proc. Int. 1992, 24, 437.
6. Iwema Bakker, W. I.; Haas, M.; Khoo-Beattie, C.; Ostaszewski, R.; Franken, S. M.; Den Hertog, Jr., H. J.; Verboom, W.; De Zeeuw, D.; Harkema, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 123.
7. Rudkevich, D.M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683.
8. Van Loon, J.-D.; Heida, J. F.; Verboom, W.; Reinhoudt, D. N. Recl. Trav. Chim. Pays-Bas 1992, 111, 353.
9. Cobben, P. L. H. M.; Egberink, R. J. M.; Bomer, J. G.; Bergveld, P.; Verboom, W.; Reinhoudt, D.N. J. Am. Chem. Soc. 1992, 114, 10573.
10. Nijenhuis, W.F.; Buitenhuis, E. G.; De Jong, F.; Sudhölter, E. J. R.; Reinhoudt, D. N. J. Am. Chem. Soc. 1991, 113, 7963.
11. Iwema Bakker, W. I.; Haas, M.; Den Hertog, Jr., H. J.; Verboom, W.; De Zeeuw, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972.
12. Arduini, A.; Pochini, A.; Reverberi, S.; Ungaro, R. J. Chem. Soc., Chem. Commun. 1984, 981.
13. (a) Shinkai, S.; Araki, K.; Koreishi, H.; Tsubaki, T.; Manabe, O. Chem. Lett. 1986, 1351.
14. (b) Sato, N.; Yoshida, I.; Shinkai, S. Chem. Lett. 1993, 1261.
15. (c) Morozumi, T.; Shinkai, S. Chem. Lett. 1994, 1515.
16. (d) Morozumi, T.; Shinkai, S. J. Chem. Soc,. Chem. Commun. 1994, 1219.
17. (a) Shinkai, S.; Araki, K.; Manabe, O. J. Chem. Soc., Chem. Commun. 1988, 187.
18. (b) Shinkai, S.; Kawabata, H.; Arimura, T.; Matsuda, T.; Satoh, H.; Manabe, O. J. Chem. Soc., Perkin Trans, 1 1989, 1073.
19. (c) Shinkai, S.; Arimura, T.; Araki, K.; Kawabata, H.; Satoh, H.; Tsubaki, T.; Manabe, O.; Sunamoto, J. J. Chem. Soc., Perkin Trans. 1 1989, 2039.
20. (d) Arena, G.; Cali, R.; Lombardo, G. G.; Rizzarelli, E.; Sciotto, D.; Ungaro, R.; Casnati, A. Supramol. Chem. 1992, 1, 19.
21. (e) Casnati, A.; Ting, Y.; Berti, D.; Fabbi, M.; Pochini, A.; Ungaro, R.; Sciotto, D.; Lombardo, G. G. Tetrahedron 1993, 49, 9815.
22. (f) Arena, G.; Bonomo, R.P.; Cali, R.; Gulino, F.G.; Lombardo, G. G.; Sciotto, D.; Ungaro, R.; Casnati, A. Supramol. Chem. 1995, 4, 287.
23. Almi, M.; Arduini, A.; Casnati, A.; Pochini, A.; Ungaro, R. Tetrahedron 1989, 45, 2177.
24. (a) Shinkai, S.; Shirahama, Y.; Tsubaki, T.; Manabe, O. J. Am. Chem. Soc. 1989, 111, 5477.
25. (b) Shinkai, S.; Shirahama, Y.; Tsubaki, T.; Manabe, O. J. Chem. Soc., Perkin Trans. 1 1989, 1859.
26. (c) Arimori, S.; Nagasaki, T.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1995, 679.
27. Steed, J. W.; Juneja, R. K.; Atwood, J. L. Angew. Chem. 1994, 106, 2571; Angew. Chem., Intl. Ed. Engl. 1994, 33, 2456.
28. Steed, J. W.; Juneja, R. K.; Atwood, J. L. Angew. Chem. 1994, 106, 2571; Angew. Chem., Intl. Ed. Engl. 1994, 33, 2456.
29. Steed, J. W.; Johnson, C. P.; Barnes, C. L.; Juneja, R. K.; Atwood, J. L.; Reilly, S.; Hollis, R. L.; Smith, P. H.; Clark, D. L. J. Am. Chem. Soc. 1995, 117, 11426.
30. Shinkai, S.; Araki, K.; Grootenhuis, P. D. J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1991, 1883.
31. Newkome, G. R.; Hu, Y.; Saunders, M. J.; Fronczek, F. R. Tetrahedron Lett. 1991, 32, 1133.
32. Shi, Y.; Zhang, Z. J. Incl. Phenom. Mol. Recog. Chem. 1994, 18, 137.
33. Marra, A.; Scherrmann, M.-C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R. Angew. Chem. 1994, 106, 2533; Angew. Chem., Intl. Ed. Engl. 1994, 33, 2479.
34. Marra, A.; Scherrmann, M.-C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R. Angew. Chem. 1994, 106, 2533; Angew. Chem., Intl. Ed. Engl. 1994, 33, 2479.
35. (a) Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 37, 5155.
36. (b) Meunier, S. J.; Roy, R. Tetrahedron Lett. 1996, 37, 5469.
37. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602.
38. A small part of this work has been published as a preliminary communication; Grote Gansey, M. H. B.; Verboom, W.; Reinhoudt, D. N. Tetrahedron Lett. 1994, 35, 7127.
39. 2 as eluent.
40. (a) Van Dienst, E.; Snellink, B. H. M.; Von Piekartz, I.; Grote Gansey, M. H. B.; Venema, F.; Feiters, M. C.; Nolte, R. J. M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6537, and references cited therein.
41. (b) Van Dienst, E.; Snellink, B. H. M.; Von Piekartz, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1151.
42. In principle, a three-step route comprising selective N-protection of tris(hydroxymethyl)aminomethane followed by O-alkylation and deprotection could also lead to the desired product, but the present route is preferred because only two steps are necessary and there is only one reactive group present under the conditions of each step.
43. Aizpurua, J.M.; Palomo, C. Tetrahedron Lett. 1985, 26, 475.
44. 2 were not successful.
45. Amines are not effectively silylated under these conditions; the N-TBDMS bond is not very stable in aqueous solutions: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York 1991; p 77, and ref 26.
46. Corey, E. J.; Yi, K. Y. Tetrahedron Lett. 1992, 33, 2289.
47. Arimori, S.; Nagasaki, T.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1995, 679.