Bridging of resorcin[4]arenes in the chair conformation to cavitands having two pairs of axial and equatorial substituents

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8259-8265

  Middel, Oskar ^a   Verboom, Willem ^a   Hulst, Ron ^a   Kooijman, Huub ^b   Spek, Anthony L ^b   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CAVITAND; RESORCIN[4]ARENE DERIVATIVE; RESORCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0032514992     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9810258     Document Type: Article

References (26)

1. For reviews, see: (a) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1994. (b) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
2. For reviews, see: (a) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests. In Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1994. (b) Timmerman, P.; Verboom, W.; Reinhoudt, D. N. Tetrahedron 1996, 52, 2663.
3. (a) Sorrell, T. N.; Pigge, F. C. J. Org. Chem. 1993, 58, 155.
4. (b) Boerrigter, H.; Lugtenberg, R. J. W.; Egberink, R. J. M.; Verboom, W.; Reinhoudt, D. N.; Spek, A. L. Gazz. Chim. Ital. 1997, 127, 709.
5. (a) Boerrigter, H.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1997, 62, 7148.
6. (b) Boerrigter, H.; Verboom, W.; Reinhoudt, D. N. Liebigs Ann. / Rec. 1997, 2247.
7. Boerrigter, H.; Grave, L.; Nissink, J. W. M.; Chrisstoffels, L. A. J.; van der Maas, J. H.; Verboom, W.; de Jong, F.; Reinhoudt, D. N. J. Org. Chem. 1998, 63, 4174.
8. Högberg, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046.
9. Weinelt, F.; Schneider, H.-J. J. Org. Chem. 1991, 56, 5527.
10. 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.
11. When the more polar boronic acid substituted benzaldehyde was condensed with 2-methylresorcinol in a 2:1 mixture of ethanol and HCI (37% in water), a mixture of chair and crown conformers was obtained, which was due to the higher solubility of both products. Lewis, P. T.; Davis, C. J.; Saraiva, M. C.; Treleaven, W. D.; McCarley, T. D.; Strongin, R. M. J. Org. Chem. 1997, 62, 6110.
12. For a recent example, see: Curtis, A. D. M. Tetrahedron Lett. 1997, 38, 4295.
13. 2b,3,4
14. Abis, L.; Dalcanale, E.; du Vosel, A.; Spera, S. J. Chem. Soc., Perkin Trans. 2 1990, 2075.
15. Because the substituent-methine bonds have the ability to rotate through the ring during cavitand formation and because the chair conformer of a resorcin[4]arene has lower rim methyl substituents, this conformer can be fully bridged to a cavitand with all the substituents in the axial orientation. Moran, J. R.; Karbach, S.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 5826.
16. Tucker, J. A.; Knobler, C. B.; Trueblood, K. N.; Cram, D. J. J. Am. Chem. Soc. 1989, 111, 3688.
17. Lippmann, T.; Wilde, H.; Pink, M.; Schafer, A.; Hesse, M.; Mann, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1195.
18. 5 in a NOESY experiment with 4, an exchange cross-signal was observed between the resonances of both different methyl groups when the reaction conditions used for cavitand synthesis were applied. This may be explained by a planar anion, formed by deprotonation at the acidic methine position, in which both methyl groups are magnetically equivalent.
19. Timmerman, P.; Boerrigter, H.; Verboom, W.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. J. Inclusion Phenom. Mol. Recognit. Chem. 1995, 18, 1.
20. Reddy, D. S.; Craig, D. C.; Desiraju, G. R. J. Am. Chem. Soc. 1996, 118, 4090.
21. (a) Jeener, J.; Meier, B. H.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
22. (b) Neuhaus, D.; Williamson, M. In The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH Publishers: Cambridge, 1989.
23. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811.
24. Bax, A.; Davis, D. J. Magn. Reson. 1985, 65, 355.
25. Bax, A.; Freeman, R. J. Magn. Reson. 1981, 44, 542.
26. States, D. J.; Haberkorn, R. A.; Ruben, D. J. J. Magn. Reson. 1982, 48, 286.