Templation in the Formation of Carceplexes

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 4103-4110

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

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000634578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9803582     Document Type: Article

References (23)

1. Comprehensive Supramolecular Chemistry; Lehn, J.-M., Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: New York, 1996.
2. (a) Cram, D. J.; Karbach, S.; Kim, Y. H.; Baczynskyj, L.; Kalleymeyn, G. W. J. Am. Chem. Soc. 1985, 107, 2575-2576.
3. (b) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests, from the series Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1994.
4. (c) Sherman, J. C. Tetrahedron 1995, 51, 3395-3422.
5. (d) Sherman, J. C. In Large Ring Compounds; Semlyen, J. A., Ed.; John Wiley & Sons, Ltd.: London, 1996; pp 507-524.
6. (e) Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1997, 119, 3229-3244.
7. (f) Helgeson, R. C.; Paek, K.; Knobler, C. B.; Maverick, E. F.; Cram, D. J. J. Am. Chem. Soc. 1996, 118, 5590-5604.
8. (g) van Wageningen, A. M. A.; Timmerman, P.; van Duynhoven, J. P. M.; Verboom, W.; van Veggel, F. C. J. M.; Reindoudt, D. N. Chem. Eur. J. 1997, 3, 639-654.
9. Chapman, R. G.; Sherman, J. C. Tetrahedron 1997, 53, 15911-15946, and references therein.
10. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204.
11. Chapman, R. G.; Chopra, N.; Cochien, E. D.; Sherman, J. C. J. Am. Chem. Soc. 1994, 116, 369-370.
12. Abbreviations: NMP, N-methylpyrrolidinone; GDS, guest-determining step (the GDS is also the product-determining step; we use GDS because our focus is on the guest or template effect in the assembly process); DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DMA, dimethylacetamide; CPK, Corey-Pauling-Koltun space filling models; Δδd, the difference in chemical shifts, usually between free and entrapped guests; MALDI, matrix-assisted laser desorption ionization.
13. 6.
14. Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1995, 117, 9081-9082.
15. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum: New York, 1990; p 120.
16. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: New York, 1988, see Chapter 2 and the Appendix.
17. Hildebrand, J. H.; Prausnitz, J. M.; Scott, R. L. Regular and Related Solutions; Van Nostrand Reinhold Co.: New York, 1970; pp 27, 213-215.
18. Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N.; Sherman, J. C.; Chapman, R. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1997, 119, 4321-4322.
19. 1H NMR spectra are simpler with methyl feet and create a larger open window to observe entrapped guest. (2) Although solubility was feared to be a problem, carceplex 2b·guest is actually more soluble in chloroform than carceplex 2a·guest. (3) Crystals grown from methyl-footed carceplexes are far more stable, and their X-ray crystal structures are easier to solve.
20. Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman, J. C. J. Org. Chem. 1995, 60, 1207-13.
21. Chapman, R. G.; J.; Sherman, J. C. Unpublished results.
22. Chopra, N.; Sherman, J. C. Supramol. Chem. 1995, 5, 31-7.
23. A derivative of compound 7 where the pendent groups are phenethyls has been reported: Kurdistani, S. K.; Robbins, T. A.; Cram. D. J. J. Chem. Soc., Chem Commun. 1995, 1259-1260.