Oxidation of nitroxyl radicals: Electrochemical and computational studies

Tetrahedron Letters

Volumn 53, Issue 16, 2012, Pages 2070-2073

  Shibuya, Masatoshi ^a   Pichierri, Fabio ^a   Tomizawa, Masaki ^a   Nagasawa, Shota ^a   Suzuki, Iwao ^b   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b TAKASAKI UNIVERSITY OF HEALTH AND WELFARE   (Japan)

Author keywords

Cyclic voltammetry; DFT calculation; Nitroxyl radical; Organocatalysis; Redox potential

Indexed keywords

ADAMANTANE DERIVATIVE; ALCOHOL; AMMONIUM DERIVATIVE; BICYCLO COMPOUND; NITRO DERIVATIVE; RADICAL;

ARTICLE; CATALYSIS; CATALYST; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ENERGY; OXIDATION; OXIDATION REDUCTION POTENTIAL; REACTION ANALYSIS;

EID: 84858442848     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.033     Document Type: Article

References (49)

1. J.M. Bobbitt, and M.C.L. Flores Heterocycles 27 1988 509 533
2. A.E.J. de Nooy, A.C. Besemer, and H. van Bekkum Synthesis 1996 1153 1174
3. R.A. Sheldon, and I.W.C.E. Arends Adv. Synth. Catal. 346 2004 1051 1071
4. T. Vogler, and A. Studer Synthesis 2008 1979 1993
5. J.M. Bobbitt, C. Brückner, and N. Merbouh Org. React. 74 2009 103 424
6. R. Ciriminna, and M. Pagliaro Org. Proc. Res. Dev. 14 2010 245 251
7. L. Tebben, and A. Studer Angew. Chem., Int. Ed. 50 2011 5034 5068
8. P.L. Anelli, C. Biffi, F. Montanari, and S. Quici J. Org. Chem. 52 1987 2559 2562
9. P.L. Anelli, S. Banfi, F. Montanari, and S. Quici J. Org. Chem. 54 1989 2970 2972
10. A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, and G. Piancatelli J. Org. Chem. 62 1997 6974 6977
11. C. Bolm, A.S. Magnus, and J.P. Hildebrand Org. Lett. 2 2000 1173 1175
12. R.A. Miller, and R.S. Hoerrner Org. Lett. 5 2003 285 287
13. M.F. Semmelhack, C.R. Schmid, D.A. Cortés, and C.S. Chou J. Am. Chem. Soc. 106 1984 3374 3376
14. P. Gamez, I.W.C.E. Arends, J. Reedijk, and R.A. Sheldon Chem. Commun. 2003 2414 2415
15. R.H. Liu, X.M. Liang, C.Y. Dong, and X.Q. Hu J. Am. Chem. Soc. 126 2004 4112 4113
16. X. He, Z. Shen, W. Mo, N. Sun, B. Hu, and X. Hu Adv. Synth. Catal. 351 2009 89 92
17. S. Wertz, and A. Studer Adv. Synth. Catal. 353 2011 69 72
18. J.M. Hoover, and S.S. Stahl J. Am. Chem. Soc. 133 2011 16901 16910
19. J.A. Cella, J.A. Kelley, and E.F. Kenehan J. Org. Chem. 40 1975 1860 1862
20. S.D. Rychnovsky, and Vaidyanathan J. Org. Chem. 64 1999 310 312
21. L. De Luca, G. Giacomelli, and A. Porcheddu Org. Lett. 3 2001 3041 3043
22. M. Shibuya, M. Tomizawa, I. Suzuki, and Y. Iwabuchi J. Am. Chem. Soc. 128 2006 8412 8413
23. M. Shibuya, T. Sato, M. Tomizawa, and Y. Iwabuchi Chem. Commun 2009 1739 1741
24. M. Shibuya, Y. Sasano, M. Tomizawa, T. Hamada, M. Kozawa, N. Nagahama, and I. Iwabuchi Synthesis 2011 3418 3425
25. M. Shibuya, M. Tomizawa, Y. Sasano, and Y. Iwabuchi J. Org. Chem. 74 2009 4619 4622
26. M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa, and Y. Iwabuchi J. Am. Chem. Soc. 133 2011 6497 6500
27. M.F. Semmelhack, C.R. Schmid, and D.A. Cortes Tetrahedron Lett. 27 1986 1119 1122
28. W.F. Bailey, J.M. Bobbitt, and K.B. Wiberg J. Org. Chem. 72 2007 4504 4509
29. Z.-W. Mei, T. Omote, M. Mansour, H. Kawafuchi, Y. Takaguchi, A. Jutand, S. Tsuboi, and T. Inokuchi Tetrahedron 64 2008 10761 10766
30. W. Sümmermann, and U. Deffner Tetrahedron 31 1975 593 596
31. M.F. Semmelhack, C.S. Chou, and D.A. Cortes J. Am. Chem. Soc. 105 1983 4492 4494
32. M.F. Semmelhack, and C.R. Schmid J. Am. Chem. Soc. 105 1983 6732 6734
33. F. MacCorquodale, J.A. Crayston, J.C. Walton, and D.J. Worsfold Tetrahedron Lett. 31 1990 771 774
34. T. Ono, M. Tsunoda, S. Takahashi, T. Obata, T. Sone, and Y. Kashiwagi Heterocycles 81 2010 2771 2780
35. M.S. Workentin, and D.D.M. Wayner Res. Chem. Intermed. 19 1993 777 785
36. R. Benassi, P. Ferrarini, C. Fontanesi, L. Benedetti, and F. Paolucci J. Electroanal. Chem. 564 2004 231 237
37. M. Shamsipur, A. Siroueinejad, B. Hemmateenejad, A. Abbaspour, H. Sharghi, K. Alizadeh, and S. Arshadi J. Electroanal. Chem. 600 2007 345 358
38. K. Alizadeh, S. Seyyedi, and M. Shamsipur Polish J. Chem. 82 2008 1449 1456
39. S.D. Rychnovsky, R. Vaidyanathan, T. Beauchamp, R. Lin, and P.J. Farmer J. Org. Chem. 64 1999 6745 6749
40. J.P. Blinco, J.L. Hodgson, B.J. Morrow, J.R. Walker, G.D. Will, M.L. Coote, and S.E. Bottle J. Org. Chem. 73 2008 6763 6771
41. S. Manda, I. Nakanishi, K. Ohkubo, H. Yakumaru, K. Matsumoto, T. Ozawa, N. Ikota, S. Fukuzumi, and K. Anzai Org. Biomol. Chem. 5 2007 3951 3955
42. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian, Inc. Wallingford CT
43. C. Adamo, and V. Barone J. Chem. Phys. 110 1999 6158 6170
44. M.M. Francl, W.J. Pietro, W.J. Hehre, J.S. Binkley, M.S. Gordon, D.J. DeFrees, and J.A. Pople J. Chem. Phys. 77 1982 3654 3665
45. R. Ditchfield, W.J. Hehre, and J.A. Pople J. Chem. Phys. 54 1971 724 728
46. J. Tomasi, B. Mennucci, and R. Cammi Chem. Rev. 105 2005 2999 3094
47. AZADO (1), 1-Me-AZADO (2), 5-F-AZADO (5) and ABNO (10) were examined.
48. R.L. Donkers, and D.G. Leaist J. Phys. Chem. B 101 1997 304 408
49. R.E. Sioda, and B. Frankowska J. Electroanal. Chem. 612 2008 147 150