The effect of substituents on the anodic oxidation of aliphatic carboxylates and the passage towards a pseudo-Kolbe reaction

Journal of Electroanalytical Chemistry

Volumn 672, Issue , 2012, Pages 28-33

  Galicia, Mónica ^a,b   González Fuentes, Miguel A ^a   Valencia, Drochss P ^a   González, Felipe J ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DE CIUDAD JUÁREZ   (Mexico)

Author keywords

Carbocations; Carboxylates; Dimers; N acylamides; Pseudo Kolbe reaction

Indexed keywords

ACETONITRILE; ANODIC OXIDATION; CYTOTOXICITY; DIMERS; ELECTROCHEMICAL OXIDATION; ELECTRON TRANSITIONS; ELECTRON TRANSPORT PROPERTIES; FREE RADICAL REACTIONS; FREE RADICALS; GLASS MEMBRANE ELECTRODES; VOLATILE FATTY ACIDS;

ACTIVATION STEPS; ALIPHATIC CARBOXYLATE; CARBOCATIONS; CARBOXYLATE GROUPS; CARBOXYLATES; CHLOROACETATE; DECARBOXYLATION REACTIONS; DISSOCIATIVE ELECTRON TRANSFERS; ELECTRON TRANSFER; GLASSY CARBON ELECTRODES; HEXANOATE; HIGH RATE; MIXED KINETICS; N-ACYLAMIDES; ONE-ELECTRON TRANSFER; PSEUDO-KOLBE REACTION; TETRABUTYLAMMONIUM;

CARBOXYLATION;

EID: 84859480379     PISSN: 15726657     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jelechem.2012.03.001     Document Type: Article

References (34)

1. H.J. Shäfer Topics in Current Chemistry 152 1990 90
2. H. Lund, and O. Hammerich Organic Electrochemistry 2001 M. Dekker
3. S. Torii Electrochemistry in Organic Synthesis 1997 Pergamon Press
4. J.H.P. Utley Technics in Electroorganic Synthesis vol. 5 1974 Wiley (Part I)
5. L. Eberson, and J.H.P. Utley M.M. Baizer, H. Lund, Organic Electrochemistry 1983 Marcel Dekker New York
6. A.J. Fry Topics in Organic Electrochemistry 1989 Wiley New York
7. A.K. Vijh, and B.E. Conway Chem. Rev. 67 1967 623
8. L. Eberson Acta Chem. Scand. 17 1963 2004
9. A.A. Isse, A. Gennaro, and F. Maran Acta Chem. Scand. 53 1999 1013
10. M. Galicia, and F.J. González J. Electrochem. Soc. 149 2002 D46
11. C.P. Andrieux, F. González, and J.M. Savéant J. Electroanal. Chem. 498 2001 171
12. C.P. Andrieux, F. Gonzalez, and J.M. Savéant J. Am. Chem. Soc. 119 1997 4292
13. T.M. Krygowski, and B.T. Stepień Chem. Rev. 105 2005 3482
14. J.A. Bautista-Martínez, I. González, and M. Aguilar-Martínez Electrochim. Acta 48 2003 4239
15. J.P. Coleman, and L. Eberson J. Chem. Soc. D 1971 1300
16. J.P. Coleman, R. Lines, J.H.P. Utley, and B.C.L. Weedon J. Chem. Soc., Perkin Trans. II 1974 1064
17. J.M. Bobbitt, and T.Y. Cheng J. Org. Chem. 41 1976 443
18. S. Antonello, and F. Maran Chem. Soc. Rev. 34 2005 418
19. L.S. Hernández-Muñoz, and F.J. González Electrochem. Commun. 13 2011 701
20. L.S. Hernández-Muñoz, M.A. González-Fuentes, B.R. Díaz, R. Fragoso, C. Vázquez-López, and F.J. González Electrochim. Acta 63 2012 287
21. J.W. Hilborn, and J.A. Pincock J. Am. Chem. Soc. 113 1991 2683
22. T.M. Bockman, S.M. Hubig, and J.K. Kochi J. Am. Chem. Soc. 118 1996 4502
23. J.M. Savéant Adv. Phys. Org. Chem. 35 2000 117
24. L. Nadjo, and J.-M. Savéant J. Electroanal. Chem. 48 1973 113
25. D.D.M. Wayner, D.J. McPhee, and D. Griller J. Am. Chem. Soc. 110 1988 132
26. B.A. Sim, P. Milne, D. Griller, and D.D.M. Wayner J. Am. Chem. Soc. 112 1990 6635
27. J. March Advanced Organic Chemistry 1992 Wiley NY pp 970-971
28. T. Yamamoto, M. Hori, I. Watanabe, H. Tsutsui, S. Ikeda, and H. Othaka Chem. Pharm. Bull. 47 1999 22
29. E. Anxolabéhre, P. Hapiot, and J.-M. Savéant J. Electroanal. Chem. 282 1990 275
30. J.M. Kornprobst, A. Laurent, and E. Laurent-Dieuzeide Bull. Soc. Chim. Fr. 9 1968 3657
31. www.gaussian.com.
32. M.N. Paddon-Row Adv. Phys. Org. Chem. 38 2003 1
33. K.D. Jordan, and M.N. Paddon-Row Chem. Rev. 92 1992 395
34. R.M. Williams, M. Koeberg, J.M. Lawson, Y.Z. An, Y. Rubin, M.N. Paddon-Row, and J.W. Verhoeven J. Org. Chem. 61 1996 5055