Incorporation of ring nitrogens into diphenylamine antioxidants: Striking a balance between reactivity and stability

Journal of the American Chemical Society

Volumn 134, Issue 20, 2012, Pages 8306-8309

  Hanthorn, Jason J ^a   Valgimigli, Luca ^b   Pratt, Derek A ^a,c  

^a QUEEN S UNIVERSITY   (Canada)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; ARYL RINGS; H-ATOM TRANSFER; NITROGEN ATOM; OXIDATION POTENTIALS;

NITROGEN;

ANILINE;

ANTIOXIDANT; DIPHENYLAMINE; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION REDUCTION POTENTIAL; SYNTHESIS;

EID: 84861413606     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300086z     Document Type: Article

References (26)

1. Ingold, K. U. Chem. Rev. 1961, 61, 563-589
2. Pratt, D. A.; DiLabio, G. A.; Valgimigli, L.; Pedulli, G. F.; Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 11085-11092
3. Mulder, P.; Korth, H.-G.; Pratt, D. A.; DiLabio, G. A.; Valgimigli, L.; Pedulli, G. F.; Ingold, K. U. J. Phys. Chem. A 2005, 109, 2647-2655
4. Brownlie, I. T.; Ingold, K. U. Can. J. Chem. 1966, 44, 861-868
5. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1963, 41, 1744-1751
6. Lucarini, M.; Pedrielli, P.; Pedulli, G. F.; Cabiddu, S.; Cipollone, M. J. Org. Chem. 1996, 61, 9259-9263
7. Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194-201
8. Pratt, D. A.; DiLabio, G. A.; Brigati, G.; Pedulli, G. F.; Valgimigli, L. J. Am. Chem. Soc. 2001, 123, 4625-4626
9. Wijtmans, M.; Pratt, D. A.; Valgimigli, L.; DiLabio, G. A.; Pedulli, G. F.; Porter, N. A. Angew. Chem., Int. Ed. 2003, 42, 4370-4373
10. Nam, T.-g.; Rector, C. L.; Kim, H.-y.; Sonnen, A. F.-P.; Meyer, R.; Nau, W. M.; Atkinson, J.; Rintoul, J.; Pratt, D. A.; Porter, N. A. J. Am. Chem. Soc. 2007, 129, 10211-10219
11. Lucarini, M.; Pedrielli, P.; Pedulli, G. F.; Valgimigli, L.; Gigmes, D.; Tordo, P. J. Am. Chem. Soc. 1999, 121, 11546-11553
12. Anderson, K. W.; Tundel, R. E.; Ikawa, T.; Altman, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 6523-6527
13. Nara, S. J.; Jha, M.; Brinkhorst, J.; Zemanek, T. J.; Pratt, D. A. J. Org. Chem. 2008, 73, 9326-9333
14. Kim, J.; Chang, S. Chem. Commun. 2008, 3052-3054
15. Murrall, N. W.; Welch, A. J. J. Organomet. Chem. 1986, 301, 109-130
16. Norton, D. M.; Mitchell, E. A.; Botros, N. R.; Jessop, P. G.; Baird, M. C. J. Org. Chem. 2009, 74, 6674-6680
17. Jha, M.; Pratt, D. A. Chem. Commun. 2008, 1252-1254
18. Hanthorn, J. J.; Pratt, D. A. J. Org. Chem. 2012, 77, 276-284
19. Howard, J. A.; Furimsky, E. Can. J. Chem. 1973, 51, 3738-3745
20. Abraham, M. H.; Grellier, P. D.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 699-711
21. Litwinienko, G.; Ingold, K. U. Acc. Chem. Res. 2007, 40, 222-230
22. DiLabio, G. A.; Johnson, E. R. J. Am. Chem. Soc. 2007, 129, 6199-6203
23. Valgimigli, L.; Amorati, R.; Petrucci, S.; Pedulli, G. F.; Hu, D.; Hanthorn, J. J.; Pratt, D. A. Angew. Chem., Int. Ed. 2009, 48, 8348-8351
24. Lias, S. G. In NIST Chemistry WebBook; Linstrom, P. J.; Mallard, W. G., Eds.; NIST Standard Reference Database 69; National Institute of Standards and Technology: Gaithersburg, MD.
25. Jensen, R. K.; Korcek, S.; Zinbo, M.; Gerlock, J. L. J. Org. Chem. 1995, 60, 5396-5400
26. Amorati, R.; Pedulli, G. F.; Pratt, D. A.; Valgimigli, L. Chem. Commun. 2010, 46, 5139-5141). The greater access to stable but electronically distinct diarylamines described here should aid in the design of experiments aimed at distinguishing which mechanism is responsible for this highly relevant catalytic activity