Efficient homogeneous radical-anion chain reactions initiated by dissociative electron transfer to 3,3,6,6-tetraaryl-1,2-dioxanes

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 178-188

  Stringle, Donald L B ^a   Magri, David C ^b   Workentin, Mark S ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

^b ACADIA UNIVERSITY   (Canada)

Author keywords

Cyclic voltammetry; Electron transfer; Endoperoxides; Fragmentation; Radical ions

Indexed keywords

ARYL SUBSTITUENTS; CHAIN REACTION; CONSTANT POTENTIAL ELECTROLYSIS; CONTROLLED POTENTIAL ELECTROLYSIS; CYCLIC VOLTAMMOGRAMS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DIGITAL SIMULATION; DISSOCIATIVE ELECTRON TRANSFERS; DISSOCIATIVE PATHWAYS; ELECTRON TRANSFER; ENDOPEROXIDES; FRAGMENTATION; HETEROGENEOUS KINETICS; INERT ELECTRODES; METHOXY; POTENTIAL DEPENDENCE; PRODUCT RATIOS; RADICAL ANIONS; RADICAL IONS;

BEARINGS (STRUCTURAL); COMPUTER CRIME; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTROLYSIS; ELECTRON TRANSITIONS; ETHERS; FREE RADICAL REACTIONS; NEGATIVE IONS; OLEFINS; PHOTODISSOCIATION; RATE CONSTANTS; SUBSTITUTION REACTIONS;

CYCLIC VOLTAMMETRY;

ANION; DIOXANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION;

ANIONS; DIOXANES; ELECTRON TRANSPORT; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 73949136067     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902023     Document Type: Article

References (63)

1. Z.V. Todres, Organic Ion Radicals: Chemistry and Applications, Marcel Dekker, NewYork, 2003.
2. L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer, Heidelberg, 1987.
3. J. P. Stevenson, W. E Jackson, J. M. Tanko, J. Am. Chem. Soc. 2002, 124, 4271.
4. J. M. Tanko, J. P. Phillips, J. Am. Chem. Soc. 1999,121, 6078.
5. M. Chahma, X. Li, P. Phillips, P. Schwartz, L. E. Brammer, Y Wang, J. M. Tanko, J. Phys. Chem. A 2005, 109, 3372.
6. J. M. Tanko, X. Li, M. Chahma, W. F Jackson, J. N Spencer, J. Am. Chem. Soc. 2007, 129, 4181.
7. D. C. Magri, M. S. Workentin, Org. Biomol. Chem. 2008, 6, 3354.
8. D. C. Magri, M. S. Workentin, Chem. Eur. J. 2008, 14, 1698.
9. E.L. Clennan, C. Foote in Organic Peroxides (Ed.: W. Ando), Wiley, New York, 1992.
10. K. J. McCullough, M. Nojima, Curr. Org. Chem. 2001, 5, 601.
11. a) D. A. Casteel, Nat. Prod. Rep. 1999,16, 55;
12. b) D. A. Casteel, Nat. Prod. Rep. 1992, 9, 289.
13. a) S. R. Meshnick, T. E. Taylor, S. Kamchonwongpaisan, Microbiol. Rev. 1996, 60, 301;
14. b) A. Robert, B. Meunier, Chem. Soc. Rev. 1998, 27, 273;
15. c) C.W. Jefford, Curr. Med. Chem. 2001, 8, 1803;
16. d) A. Robert, O. Dechy-Cabaret, J. Cazelles, B. Meunier, Acc. Chem. Res. 2002, 35,167;
17. e) P. M. O'Neill, G. H. Posner, J. Med. Chem. 2004, 47, 2945;
18. f) P. M. O'Neill, G H. Posner, Acc. Chem. Res. 2004, 37, 397.
19. C. Thebtaranonth, Y Thebtaranonth, S. Wanauppathamkul, Y Yu- thavong, Phytochemistry 1995, 40, 125.
20. a) S. Sperry, F A. Valeriote, T. H. Corbett, P Crews, J. Nat. Prod. 1998, 61, 241;
21. b) K. ElSayed, M. T. Hamann, N.E. Hashish, T. Shier, M. Kelly, A. A. Khan, J. Nat. Prod. 2001, 64, 522;
22. c) Y-C. Shen, C. V. S. Prakash, Y-H. Kuo, J. Nat. Prod. 2001, 64, 324;
23. d) D. T. A. Youssef, W. Y Yoshida, M. Kelly, P. J. Scheuer, J. Nat. Prod. 2001, 64, 1332.
24. M. S. Workentin, F Maran, D. D. M. Wayner, J. Am. Chem. Soc. 1995,117, 2120.
25. R. L. Donkers, M. S. Workentin, J. Phys. Chem. B 1998, 102, 4061.
26. R. L. Donkers, F Maran, D. D. M. Wayner, M. S. Workentin, J. Am. Chem. Soc. 1999,121, 7239.
27. M. S. Workentin, R. L. Donkers, J. Am. Chem. Soc. 1998, 120, 2664.
28. R. L. Donkers, M. S. Workentin, Chem. Eur. J. 2001, 7, 4012.
29. D. C. Magri, R. L. Donkers, M. S. Workentin, J. Photochem. Photobiol. A 2001,138, 29.
30. D. C. Magri, M. S. Workentin, Org. Biomol. Chem. 2003, 1, 3418.
31. R. L. Donkers, J. Tse, M.S. Workentin, J. Chem. Soc. Chem. Commun. 1999, 135.
32. R. L. Donkers, M. S. Workentin, J. Am. Chem. Soc. 2004, 126, 1688.
33. D. L. B. Stringle, R. N. Campbell, M. S. Workentin, J. Chem. Soc. Chem. Commun. 2003,1246.
34. F. Najjar, C. André-Barrès, C. Lacaze-Dufaure, D. C. Magri, M. S. Workentin, T. Tzèdakis, Chem. Eur. J. 2007, 13, 1174.
35. S. Antonello, M. Musumeci, D. D. M. Wayner, F. Maran, J. Am. Chem. Soc. 1997, 119, 9541.
36. S. Antonello, F. Maran, J. Am. Chem. Soc. 1997, 119, 12595.
37. S. Antonello, F. Maran, J. Am. Chem. Soc. 1999, 121, 9668.
38. S. Antonello, F. Formaggio, A. Moretto, C. Toniolo, F. Maran, J. Am. Chem. Soc. 2001, 123, 9577.
39. S. Antonello, M. Crisma, F. Formaggio, A. Moretto, F. Taddei, C. Toniolo, F. Maran, J. Am. Chem. Soc. 2002, 124,11503.
40. S. Antonello, F. Formaggio, A. Moretto, C. Toniolo, F. Maran, J. Am. Chem. Soc. 2003, 125, 2874.
41. F. Polo, S. Antonello, F. Formaggio, C. Toniolo, F. Maran, J. Am Chem. Soc. 2005, 127, 492.
42. R. Improta, S. Antonello, F. Formaggio, F. Maran, N Rega, V. Barone, J. Phys. Chem. B 2005, 109,1023.
43. Reviews: a) J.-M. Savéant in Advances in Physical Organic Chemistry, Vol.26 (Ed.: D. Bethel), Academic Press, New York, 1990, p. 1;
44. b) J.-M. Savéant, Ace. Chem. Res. 1993, 26, 455;
45. c) J.-M. Savéant in Advances in Electron Transfer Chemistry, Vol.4 (Ed.: P S. Mariano), JAI Press, Greenwich, 1994, p. 53;
46. d) J.-M. Savéant in Advances in Physical Organic Chemistry, Vol.35 (Ed.: T. Tidwell), Academic Press, New York, 2000, p. 117;
47. e) C. Costentin, M. Robert, J.-M. Savéant, Chem. Phys. 2006, 324, 40;
48. f) C. Costentin, L. Donati, M. Robert, Chem. Eur. J. 2009,15, 785.
49. Reviews: a) F Maran, D. D. M. Wayner, M. S. Workentin in Advances in Physical Organic Chemistry, Vol.36 (Ed.: T. T. Tidwell), Academic Press, New York, 2001, p. 85;
50. b) S. Antonello, F Maran, Chem. Soc. Rev. 2005, 34, 418;
51. c)R.A. Rossi, A.B. Pierini, A.B. Penenory, Chem. Rev. 2003, 103, 71;
52. d) A. Houmam, Chem. Rev. 2008,108, 2180.
53. R. K. Haynes, M. K. S. Probert, I. D. Wilmot, Aust. J. Chem. 1978, 31, 1737.
54. K. Gollnick, A. Schnatterer, Tetrahedron Lett. 1984,25,185.
55. K. Gollnick, A. Schnatterer, G Utschick, J. Org. Chem. 1993, 58, 6049.
56. K. Mizuno, T. Tamai, I. Hashida, Y Otsuji, Y Kuriyama, K. Tokumaru, J. Org. Chem. 1994, 59, 7329.
57. 1H NMR spectra it was noted that there were two unidentified resonances, comprising less than 10% of the product mixture. These may be due to arylmethoxy protons and aryl protons of a psubstituted aromatic moiety. However, the compounds were not isolated or identified.
58. One possibility that we eluded to in references [7] and [8] is that in the presence of a weak acid, protonation of the alkoxide portion could first occur, followed by reduction of the alkoxyl portion and subsequent protonation to yield diol 3.
59. a) J. C. Imbeaux, J.-M. Savéant, J. Electroanal. Chem. 1973, 44, 169;
60. b) J.-M. Savéant, D. Tessier, J. Electroanal. Chem. 1975, 61, 251.
61. W. Adam, J. Sanabia, J. Am. Chem. Soc. 1977, 99, 2735.
62. S. Antonello, R. Benassi, G Gavioli, F Taddei, F Maran, J. Am. Chem. Soc. 2002, 124, 7529.
63. S. Antonello, K. Daasbjerg, H. Jensen, F Taddei, F Maran, J. Am. Chem. Soc. 2003, 125 ,14905.