Synthesis of the phenoxonium cation of an α-tocopherol model compound crystallized with non-nucleophilic [B(C6F5) 4]- and (CB11H6Br6) - anions

Journal of the American Chemical Society

Volumn 128, Issue 29, 2006, Pages 9332-9333

  Lee, Stephen B ^a   Willis, Anthony C ^a   Webster, Richard D ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHROMANONE DERIVATIVE; ALPHA TOCOPHEROL; ANION; BORON DERIVATIVE; BROMINE DERIVATIVE; CHROMANOL; DICHLOROETHANE; FLUORINE DERIVATIVE; ORGANIC SOLVENT; PHENOL DERIVATIVE; PHENOXONIUM ION; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; METHYLATION; OXIDATION; SOLUBILITY; SYNTHESIS; X RAY DIFFRACTION;

EID: 33746375063     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0634268     Document Type: Article

References (35)

1. (a) Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194-201.
2. (b) Bowry, V. W.; Ingold, K. U. Acc. Chem. Res. 1999, 32, 27-34.
3. (a) Azzi, A.; Stocker, A. Prog. Lipid Res. 2000, 39, 231-255.
4. (b) Ricciarelli, R.; Zingg, J.-M.; Azzi, A. Biol. Chem. 2002, 383, 457-465.
5. (c) Azzi, A.; Ricciarelli, R.; Zingg J.-M. FEBS Lett. 2002, 519, 8-10.
6. (a) Boscoboinik, D.; Szewczyk, A.; Hensey, C.; Azzi, A. J. Biol. Chem. 1991, 266, 6188-6194.
7. (b) Tasinato, A.; Boscoboinik, D.; Bartoli, G. M.; Maroni, P. Azzi, A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12190-12194.
8. Min, K. C.; Kovall, R. A.; Hendrickson, W. A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 14713-14718.
9. Hosomi, A.; Arita, M.; Sato, Y.; Kiyose, C.; Ueda, T.; Igarashi, O.; Arai, H.; Inoue, K. FEBS Lett. 1997, 409, 105-108.
10. Svanholm, U.; Bechgaard, K.; Parker, V. D. J. Am. Chem. Soc. 1974, 96, 2409-2413.
11. (a) Webster, R. D. Electrochem. Commun. 1999, 1, 581-584.
12. (b) Williams, L. L.; Webster, R. D. J. Am. Chem. Soc. 2004, 126, 12441-12450.
13. (c) Lee, S. B.; Lin, C. Y.; Gill, P. M. W.; Webster, R. D. J. Org. Chem. 2005, 70, 10466-10473.
14. (d) Wilson, G. J.; Lin, C. Y.; Webster, R. D. J. Phys. Chem. B 2006, 110, 11540-11548.
15. 7b,7c
16. The chemical oxidation procedure is preferable for synthetic experiments because it avoids the requirement of supporting electrolyte.
17. The carborane was synthesized by the following procedures: (a) Dunks, G. B.; Ordonez, K. P. Inorg. Chem. 1978, 17, 1514-1516.
18. (b) Franken, A.; King, B. T.; Rudolph, J.; Rao, P.; Noll, B. C.; Michl, J. Collect. Czech. Chem. Commun. 2001, 66, 1238-1249.
19. (c) Jelinek, T.; Plesek, J.; Hermanek, S.; Stibr, B. Collect. Czech. Chem. Commun. 1986, 51, 819-829.
20. 4] was used.
21. (a) Reed, C. A.; Kim, K.-C.; Bolskar, R. D.; Mueller, L. J. Science 2000, 289, 101-104.
22. (b) Camire, N.; Nafady, A.; Geiger, W. E. J. Am. Chem. Soc. 2002, 124, 7620-7261.
23. (c) Krossing, I.; Raabe, I.; Angew. Chem., Int. Ed. 2004, 43, 2066-2090.
24. (a) Rosenau, T.; Habicher, W. D. Tetrahedron 1995, 51, 7919-7926.
25. (b) Rosenau, T.; Potthast, A.; Elder, T.; Kosma, P. Org. Lett. 2002, 4, 4285-4288.
26. (a) Lin, C. Y.; George, M. W.; Gill, P. M. W. Aust. J. Chem. 2004, 57, 365-370.
27. (b) Gill, P. M. W.; Johnson, B. G.; Pople, J. A. Chem. Phys. Lett. 1993, 209, 506-512.
28. (a) Hammerich, O.; Svensmark, B. In Organic Electrochemistry, 3rd ed.; Lund, H., Baizer, M. M., Eds.; Marcel Dekker: New York, 1991; Chapter 16.
29. (b) Rieker, A.; Beisswenger, R.; Regier, K. Tetrahedron 1991, 47, 645-654.
30. (c) Eickhoff, H.; Jung, G.; Rieker, A. Tetrahedron 2001, 57, 353-364.
31. (a) Speiser, B.; Rieker, A. J. Chem. Res. (S) 1977, 314-315.
32. (b) Speiser, B.; Rieker, A. J. Chem. Res. (M) 1977, 3601-3618.
33. (c) Speiser, B.; Rieker, A. J. Electroanal. Chem. 1979, 102, 373-395.
34. (d) Speiser, B.; Rieker, A. J. Electroanal. Chem. 1980, 110, 231-246.
35. Vigalok, A.; Rybtchinski, B.; Gozin, Y.; Koblenz, T. S.; Ben-David, Y.; Rozenberg, H.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 15692-15693.