Synthesis of hydroxyl-footed cavitands

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1505-1509

  Gibb, Bruce C ^a   Chapman, Robert G ^a   Sherman, John C ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001002729     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951633c     Document Type: Article

References (35)

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3. (b) 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, 2229-2237. For a review of unbridged resorcinarenes, see: Schneider, H.-J.; Schneider, U. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 67-83.
4. (a) Sherman, J. C. Tetrahedron 1995, 51, 3395-3422.
5. (b) Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. Eur. 1995, 7, 132-143.
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12. For formation of monolayers using unbridged resorinarenes, see: (c) Kurihara, K.; Ohto, K.; Tanaka, Y.; Aoyama, Y.; Kunitake, T. J. Am. Chem. Soc. 1991, 113, 444-400. (d) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem, Commun. 1994, 2527-2529. (e) Weib, T.; Schierbaum, K. D.; van Velzen, U. T.; Reinhoudt, D. N.; Göpel, W. Sensors Actuat. B 1995, 26-27, 203-207.
13. For formation of monolayers using unbridged resorinarenes, see: (c) Kurihara, K.; Ohto, K.; Tanaka, Y.; Aoyama, Y.; Kunitake, T. J. Am. Chem. Soc. 1991, 113, 444-400. (d) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem, Commun. 1994, 2527-2529. (e) Weib, T.; Schierbaum, K. D.; van Velzen, U. T.; Reinhoudt, D. N.; Göpel, W. Sensors Actuat. B 1995, 26-27, 203-207.
14. For formation of monolayers using unbridged resorinarenes, see: (c) Kurihara, K.; Ohto, K.; Tanaka, Y.; Aoyama, Y.; Kunitake, T. J. Am. Chem. Soc. 1991, 113, 444-400. (d) Adams, H.; Davis, F.; Stirling, C. J. M. J. Chem. Soc., Chem, Commun. 1994, 2527-2529. (e) Weib, T.; Schierbaum, K. D.; van Velzen, U. T.; Reinhoudt, D. N.; Göpel, W. Sensors Actuat. B 1995, 26-27, 203-207.
15. For uses of resorcinarene-based cavitands that contain non-methylene bridges, see: (a) Lippmann, T.; Wilde, H.; Dalcanale, E.; Mavilla, L.; Mann, G.; Heyer, U.; Spera, S. J. Org. Chem. 1995, 60, 235-242. (b) Vincenti, M.; Dalcanale, E. J. Chem. Soc., Perkin Trans. 2 1995, 1069-1076.
16. For uses of resorcinarene-based cavitands that contain non-methylene bridges, see: (a) Lippmann, T.; Wilde, H.; Dalcanale, E.; Mavilla, L.; Mann, G.; Heyer, U.; Spera, S. J. Org. Chem. 1995, 60, 235-242. (b) Vincenti, M.; Dalcanale, E. J. Chem. Soc., Perkin Trans. 2 1995, 1069-1076.
17. (c) Xu, W.; Vittal, J. J,; Puddephatt, R. J. J. Am. Chem. Soc. 1993, 115, 6456-6457.
18. (d) Vincenti, M.; Pelizzetti, E.; Dalcanale, E.; Soncini, P. Pure Appl. Chem 1993, 65, 1507-1512.
19. (e) Sonicini, P.; Bonsignore, S.; Dalcanale, E.; Ugozzoli, F. J. Org, Chem. 1992, 57, 4608-4612.
20. (f) Dalcanale, E.; Costantini, G.; Soncini, P. J. Inclusion Phenom. Mol. Recognit. Chem. 1992, 13, 87-92.
21. (g)Xu, W., Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1995, 117, 8362-8371.
22. For linkage of cavitands to each other via their rims, see ref 2 and (a) Cram, D. J.; Tunstad, L. M.; Knobler, C. B. J. Org. Chem. 1992, 57, 528-535. (b) von dem Bussche-Hunnefeld, C.; Buhring, D.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1995, 1085-1086.
23. For linkage of cavitands to each other via their rims, see ref 2 and (a) Cram, D. J.; Tunstad, L. M.; Knobler, C. B. J. Org. Chem. 1992, 57, 528-535. (b) von dem Bussche-Hunnefeld, C.; Buhring, D.; Knobler, C. B.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1995, 1085-1086.
24. Compound 2a has been reported previously, hut was not fully characterized, see: 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, 1305-1312.
25. For the incorporation of alcohols of different chain length into the lower rim of calixarenes, see: Moran, J. K.; Georgiev, E. M.; Yordanov, A. T.; Mague, J. T.; Roundhill, D. M. J. Org. Chem. 1994, 59, 5990-5998.
26. 2, see: Cram, D. J.; Stewart, K. D.; Goldberg, I.; Trueblood, K. N. J. Am. Chem. Soc. 1985, 707, 2574-2575.
27. Emmons, W. D.; Ferris, A. F. J. Am. Chem. Soc. 1953, 75, 2257.
28. The 41% yield in the methylene bridging of octol 3c would likely increase if the MOM groups were replaced by a more robust protective group such as (methoxyethoxy) methyl.
29. Timmerman, P.; Boerrigter, H.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 167-191.
30. (a) Schneider, H.-J.; Guttes, D.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6449-6454.
31. (b) Sorrell, T. N.; Pigge, F. C.; White, P. S. Inorg. Chem. 1994, 33, 632-635.
32. 1H NMR.
33. Cavitand 4d has been prepared previously in 52% yield on a 21 g scale using similar conditions to entry 25 in Table 1, see: Sherman, J. C.; Knobler, C. N.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204.
34. For further general experimental details, see: Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman, J. C. J. Org. Chem, 1995, 60, 1207-1213.
35. For the preparation of octol 2d, see ref 7.