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Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 513-516

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

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; ENCAPSULATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; THERMODYNAMICS;

EID: 0034723219     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991433r     Document Type: Article

References (25)

1. (a) Rebek, J., Jr. Acc. Chem. Res. 1998, 32, 278-286.
2. (b) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Ace. Chem. Res. 1996, 29, 203-209.
3. (a) Kurdistani, S. K.; Robbins, T. A.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1995, 1259.
4. (b) Timmerman, P.; Verboom, W.; van Veggel, F. C. J. M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 2345-2348.
5. (c) van Wageningen, A. M. A.; Timmerman P.; van Duynhoven, J. P. M.; Verboom, W.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Chem. Eur. 1997, 3, 639-654.
6. (d) Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman, J. C. J. Org. Chem. 1995, 60, 1207-1218.
7. (e) Place, D.; Brown, J.; Deshayes, K. Tetrahedron Lett. 1998, 39, 5915-5918. See also: Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967.
8. (e) Place, D.; Brown, J.; Deshayes, K. Tetrahedron Lett. 1998, 39, 5915-5918. See also: Jasat, A.; Sherman, J. C. Chem. Rev. 1999, 99, 931-967.
9. (a) O'Leary, B. M.; Grotzfeld, R. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 11701-11702.
10. (b) Hilmersson, G.; Rebek, J., Jr. Magn. Reson., Chem. 1998, 36, 663-669.
11. (c) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. See also: Kirchhoff, P. D.; Dutasta, J.-P.; Collet, A.; McCammon, J. A. J. Am. Chem. Soc. 1999, 121, 381-390.
12. (e) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278-286. See also: Kirchhoff, P. D.; Dutasta, J.-P.; Collet, A.; McCammon, J. A. J. Am. Chem. Soc. 1999, 121, 381-390.
13. In a variety of bisbowl systems, the two cavitands are twisted with respect to one another. We have called the two enantiomeric forms twistomers: Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 1962-1963.
14. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204.
15. Yoon, J.; Sheu, C.; Houk, K. N.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1996, 61, 9323-9329.
16. Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1995, 117, 9081-9082.
17. Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 9819-9826.
18. 2 axes of the host. See ref 2b.
19. The 1a·1,4-thioxane sample was contaminated with a small amount of 1a·dioxane, due to a small impurity of dioxane in the thioxane and the much higher preference for dioxane over thioxane: see ref 11.
20. Chapman, R. G.; Sherman, J. C. J. Org. Chem. 1998, 63, 4103-4110.
21. 4.
22. Jensen, F. R.; Neese, R. A. J. Am. Chern. Soc. 1975, 97, 4922-4925. These authors report a ΔG‡ value of 8.7 kcal/mol for interconversion between the chair and the twist-chair of thioxane. By halving the rate constant, one obtains a ΔG‡ value of 9.0 kcal/mol for chair-to-chair interconversion.
23. Barnes, J. C.; Hunter, G.; Lown, M. W. J. Chem. Soc., Perkin Trans. 2 1975, 1354-1356. The authors report a ΔG‡ value of 11 kcal/ mol, but must have miscalculated, as their data are consistent with 9.0 kcal/mol, which agrees with ref 13.
24. Vergamini, P. J.; Vahrenkamp, H.; Dahl, L. F. J. Am. Chem. Soc. 1971, 93, 6329-6330.
25. Chapman, R. G.; Olovsson, G.; Trotter, J.; Sherman, J. C. J. Am. Chem. Soc. 1998, 120, 6252-6260.