Functionalized deep-cavity cavitands

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9286-9288

  Xi, Huaping ^a   Gibb, Corinne L D ^a   Gibb, Bruce C ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032776336     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909913     Document Type: Article

References (39)

1. Molenveld, P.; Stikvoort, W. M. G.; Kooijman, H.; Spek, A. L.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1999, 64, 3896-3906 and references therein.
2. Comprehensive Supramolecular Chemistry; Marie, J.-M., Ed.; Pergamon: New York, 1996.
3. Kirby, A. J. Angew. Chem., Int. Ed Engl. 1996, 35, 707-724.
4. Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 551-553.
5. Reichwein, A. M.; Verboom, W.; Reinhoudt, D. N. Rec. Trav. Chim. Pays-Bas 1994, 113, 343-349.
6. Brady, P. A.; Sanders, J. K. M. Chem. Soc. Rev. 1997, 26, 327-336.
7. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011.
8. Breslow, R.; Schmuck, C. J. Am. Chem. Soc. 1996, 118, 6601-6605.
9. Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
10. Blanchard, S.; Le Clainche, L.; Rager, M.-N.; Tuchagues, J.-P.; Dupart, A. F.; Le Mest, Y.; Reinaud, O. Angew. Chem., Int. Ed. Engl. 1998, 37, 2732-2735.
11. For calixarenes that recognize protein surfaces, see: Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8-13.
12. Ross, H.; Lüning, U. Tetrahedron Lett. 1997, 38, 4539-4542. Ross, H.; Lüning, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 2555- 2557.
13. Ross, H.; Lüning, U. Tetrahedron Lett. 1997, 38, 4539-4542. Ross, H.; Lüning, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 2555-2557.
14. Breslow, R.; Zhang, X.; Huang, Y. J. Am. Chem. Soc. 1997, 119, 4535-4536.
15. Collman, J. P.; Herrmann, P. C.; Fu, L.; Eberspacher, T. A.; Eubanks, M.; Boitrel, B.; Hayoz, P.; Zhang, X.; Brauman, J. I.; Day, V. W. J. Am. Chem. Soc. 1997, 119, 3481-3489.
16. Collman, J. P.; Rapta, M.; Bröring, M.; Raptova, L.; Schwenninger, R.; Boitrel, B.; Fu, L.; L'Her, M. J. Am. Chem. Soc. 1999, 121, 1387-1388 and references therein.
17. Kennan, A. J.; Whitlock, H. W. J. Am. Chem. Soc. 1996, 118, 3027-3028.
18. Coolen, H. K. A. C.; van Leeuwen, P. W. N. M.; Nolte, R. J. M. J. Org. Chem. 1996, 61, 4739-4747 and references therein.
19. Xi, H.; Gibb, C. L. D.; Stevens, E. D.; Gibb, B. C. Chem. Commun. 1998, 1743-1744 (and references therein for structurally related cavitands).
20. 38
21. Lansinger, J. M.; Ronald, R. C. Synth. Commun. 1979, 9, 341-349.
22. March, J. Advanced Organic Chemistry; Reactions, Mechanisms, and Structure; Wiley-Interscience: New York, 1992; pp 694 and references therein.
23. Day, G. M.; Howell, O. T.; Metzler, M. R.; Woodgate, P. D. Aust. J. Chem. 1997, 50, 425-434.
24. To the best of our knowledge, no systematic studies to determine σ values for the hydrolysis of benzal halides has been undertaken.
25. Our efforts to examine the effects of strongly electron-donating groups para to the benzal halide were thwarted by the instability of p-phenoxybenzal bromide. Thus although it is readily synthesized from the corresponding aldehyde, all attempts to isolate this bridging material met with failure.
26. Reference 21, p 280
27. 6-DMSO) showed that, after 1 day at 60 °C, 26%, 28%, 49%, and 54% of the halide had been converted to the corresponding aldehyde.
28. Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989.
29. 2C benzal bromide.
30. Kam, T. S.; Lim, T.-M. J. Chem. Soc., Perkin Trans. 2 1993, 147-150.
31. 2 in essentially quantitative yield. For further details of this chemistry see ref 35.
32. Vitullo, V. P.; Grabowski, J.; Sridharan, S. Chem. Commun. 1981, 737-734.
33. Jorge, J. A. L.; Kiyan, N. Z.; Miyata, Y.; Miller, J. J. Chem. Soc., Perkin Trans. 2 1981, 100-103.
34. Lee, I.; Sohn, S. C.; Oh, Y. J.; Lee, B. C. Tetrahedron 1998, 42, 4713-4718.
35. Anderson, E.; Capon, B. J. Chem. Soc., Perkin Trans. 2 1972, 515-522.
36. Mataka, S.; Liu, G.-B.; Sawada, T.; Kurisu, M.; Tashiro, M. Bull. Chem. Soc. Jpn. 1994, 67, 1113-1119.
37. Lee, J. G.; Seo, J. W.; Yoon, U. C.; Kang, K.-T. Bull. Korean Chem. Soc. 1995, 16, 371-374.
38. Desruet, M.-D.; Morin, C.; Ogier, L. Carbohydr. Res. 1997, 301, 225-229.
39. Mamalis, P.; Green, J.; McHale, D. J. Chem. Soc. 1960, 229-238.