Interactions of arenes and thioethers resulting in facilitated oxidation

Organic Letters

Volumn 11, Issue 2, 2009, Pages 397-400

  Chung, Woo Jin ^a   Ammam, Malika ^b,c   Gruhn, Nadine E ^a   Nichol, Gary S ^a   Singh, Waheguru P ^a   Wilson, George S ^b   Glass, Richard S ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF KANSAS   (United States)

^c UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; SULFIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTROCHEMISTRY; OXIDATION REDUCTION REACTION;

ELECTROCHEMISTRY; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; SULFIDES;

EID: 61449211129     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802683s     Document Type: Article

References (54)

1. Morgan, R. S.; Tabsch, C. E.; Gushard, R. H.; McAdon, J. M.; Warme, P. K. Int. J. Peptide Protein Res 1978, 11, 209-217.
2. Breinlinger, E. C.; Keenan, C. J.; Rotello, V. M. J. Am. Chem. Soc. 1998, 120, 8606-8609.
3. Rotello, V. M. Heteroatom Chem. 1998, 9, 605-606.
4. Low, D. W.; Hill, M. G. J. Am. Chem. Soc. 1998, 120, 11536-11537.
5. (a) Werst, D. W.; Trifunac, A. D. J. Phys. Chem. 1991, 95, 3466-3477.
6. (b) Werst, D. W. J. Am. Chem. Soc. 1991, 113, 4345-4346.
7. (c) Werst, D. W. J. Phys. Chem. 1992, 96, 3640-3646.
8. (a) Butterfield, D. A. Free Rad. Res. 2002, 36, 1307-1313.
9. (b) Butterfield, D. A.; Kanski, J. Peptides 2002, 23, 1299-1309.
10. (c) Butterfield, D. A. Curr. Med. Chem. 2003, 10, 2651-2659.
11. (d) Schöneich, C. Biochim. Biophys. Acta 2005, 1703, 111-119.
12. Varadarajan, S.; Yatin, S.; Kanski, J.; Jahanashahi, F.; Butterfield, D. A. Brain Res. Bull. 1999, 50, 133-141.
13. Pogocki, D. Chem. Res. Toxicol. 2004, 17, 325-329.
14. Boyd-Kimball, D.; Abdul, H. M.; Reed, T.; Sultana, R.; Butterfield, D. A. Chem. Res. Toxicol. 2004, 17, 1743-1749.
15. Murakami, K.; Irie, K.; Ohigashi, H.; Hara, H.; Nagao, M.; Shimizu, T.; Shirasawa, T. J. Am. Chem. Soc. 2005, 127, 15168-15174.
16. (a) Glass, R. S.; Sabahi, M.; Singh, W. P. J. Org. Chem. 1992, 57, 2683-2688.
17. (b) Creary, X.; Wang, Y-X. Res. Chem. Intermed. 1994, 20, 201-222.
18. 4, the phenolic OH group was protected with a t-butyl dimethylsilyl moiety which was removed on workup.
19. Fantin, G.; Fogagnolo, M.; Guerini, R.; Marastoni, M.; Medici, A.; Pedrini, P. Tetrahedron 1994, 50, 12973-12978.
20. Martin, H.-D.; Mayer, B. Angew. Chem., Int. Ed. 1983, 22, 283-314.
21. (a) Glass, R. S.; Broeker, J. L.; Jatcko, M. E. Tetrahedron 1989, 45, 1263-1272.
22. (b) Glass, R. S; Andruski, S. W.; Broeker, J. L.; Firouzabadi, H.; Steifen, L. K.; Wilson, G. S. J. Am. Chem. Soc. 1989, 111, 4036-4045.
23. Klasinc, L.; Kovac, B.; Güsten, H. Pure Appl. Chem. 1983, 55, 289-298.
24. Brundle, C. R.; Robin, M. B.; Kuebler, N. A. J. Am. Chem. Soc. 1972, 94, 1466-1475.
25. 22 eV).
26. Coleman, B. R.; Glass, R. S.; Setzer, W. N.; Prabhu, U. D. G.; Wilson, G. S. Adv. Chem. Ser. 1982, 201, 417-441.
27. Gleiter, R.; Spanget-Larsen, J. Top. Curr. Chem. 1979, 86, 139-195.
28. Bock, H.; Wagner, G.; Kroner, J. Chem. Ber. 1972, 105, 3850-3864.
29. Heilbronner, E.; Hornung, V.; Pinkerton, F. H.; Thames, S. F. Helv. Chim. Acta 1972, 55, 289-302.
30. 22 eV).
31. 19,20
32. (a) Hoffmann, R. Acc. Chem. Res. 1971, 4, 1-9.
33. (b) Gleiter, R. Angew. Chem., Int. Ed. 1974, 13, 696-701.
34. (c) Brunk, T. K.; Weinhold, F. J. Am. Chem. Soc. 1976, 98, 4392-4393.
35. (a) Sweigart, D. A.; Turner, D. W. J. Am. Chem. Soc. 1972, 94, 5599-5603.
36. (b) Gonbeau, D.; Loudet, M.; Pfister-Guillouzo, G. Tetrahedron 1980, 36, 381-391.
37. (c) Vondrak, T.; Basil, Z. J. Mol. Struct. 1987, 160, 117-126.
38. (a) Glass, R. S.; Block, E.; Lorance, E.; Zakai, U. I.; Gruhn, N. E.; Jin, J.; Zhang, S.-Z. J. Am. Chem. Soc. 2006, 128, 12685-12692.
39. (b) Glass, R. S.; Block, E.; Gruhn, N. E.; Jin, J.; Lorance, E.; Zakai, U. I.; Zhang, S.-Z. J. Org. Chem. 2007, 72, 8290-8297.
40. MPWB1K/6-31+G** has been shown to well describe through-space interactions:Zhao, Y.; Truhlar, D. G Phys. Chem. Chem. Phys. 2005, 7, 2701-2705.
41. 30 that sulfur-arene interactions are overall stabilizing. Thus, even though the HOMO of 1a is raised in energy, other factors likely compensate for this orbital destabilization resulting in overall stabilization of 1a.
42. (a) Viguera, A. R.; Serrano, L. Biochemistry 1995, 34, 8771-8779.
43. (b) Lomize, A. L.; Reibarkh, M. Y.; Pogozheva, I. D. Protein Sci. 2002, 11, 1984-2000.
44. (c) Zauhar, R. J.; Colbert, C. L.; Morgan, R. S.; Welsh, W. J. Biopolymers 2000, 53, 233-248.
45. (d) Meper, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
46. (e) Motherwell, W. B.; Moïse, J.; Aliev, A. B.; Nic, M.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Chessari, G.; Hunter, C. A.; Vinter, J. G. Angew. Chem., Int. Ed. 2007, 46, 7823-7826.
47. (f) Ringer, A. L; Senenko, A.; Sherrill, C. D. Protein Sci. 2007, 16, 2216-2223.
48. 2S or phenyl alone, that is, without interaction.
49. Shudo, K.; Kobayashi, T.; Utsunomiya, C. Tetrahedron 1977, 33, 1721-1724.
50. 22 eV).
51. 19
52. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2nd ed.; Wiley: New York, 2001; p 236.
53. (a) Block, E.; Glass, R. S.; DeOrazio, R.; Lichtenberger, D. L.; Pollard, J. R.; Russell, E.; Schroeder, T. B.; Thiruvazhi, M.; Toscano, P. J. Synlett 1997, 525-528.
54. (b) Block, E.; Birringer, M.; DeOrazio, R.; Fabian, J.; Glass, R. S.; Guo, C.; He, C.; Lorance, E.; Qian, Q.; Schroeder, T. B.; Shan, Z.; Thiruvazhi, M.; Wilson, G. S.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 5052-5064.