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Electrochemical Oxidation of Benzyl Alcohol on Platinum Electrode with TEMPO in CH3CN/H2O
Corresponding Author(s) : Meichao Li
Asian Journal of Chemistry,
Vol. 27 No. 9 (2015): Vol 27 Issue 9
Abstract
In situ FT-IR and cyclic voltammetry were employed to study the oxidation reaction of benzyl alcohol on platinum electrode with 2,2,6,6-tetramethylpiperidin-1-yloxy (TEMPO) in CH3CN/H2O solution containing NaClO4. Cyclic voltammograms were characterized by a well-defined one electron reversible redox couple. The possible catalytic oxidation mechanism of benzyl alcohol with TEMPO was studied using in situ FT-IR spectroscopy. It suggested that oxoammonium ion was generated by one-electron oxidation of TEMPO at low oxidation potential and benzyl alcohol was mainly oxidized to benzaldehyde instead of benzoic acid.
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References
W. Adam, C.R. Saha-Möller and P.A. Ganeshpure, Chem. Rev., 101, 3499 (2001); doi:10.1021/cr000019k.
P.L. Anelli, C. Biffi, F. Montanari and S. Quici, Org. Chem., 52, 2559 (1987); doi:10.1021/jo00388a038.
A.C. Herath and J.Y. Becker, Electrochim. Acta, 53, 4324 (2008); doi:10.1016/j.electacta.2007.12.082.
S. Kishioka, T. Ohsaka and K. Tokuda, Electrochim. Acta, 48, 1589 (2003); doi:10.1016/S0013-4686(03)00024-0.
N. Jiang and A.J. Ragauskas, Tetrahedron Lett., 46, 3323 (2005); doi:10.1016/j.tetlet.2005.03.078.
M.F. Semmelhack, C.R. Schmid, D.A. Cortes and C.S. Chou, J. Am. Chem. Soc., 106, 3374 (1984); doi:10.1021/ja00323a064.
D. Liaigre, T. Breton and E.M. Belgsir, Electrochem. Commun., 7, 312 (2005); doi:10.1016/j.elecom.2005.01.002.
R. Barhdadi, C. Comminges, A.P. Doherty, J.Y. Nedelec, S. O’Toole and M. Troupel, J. Appl. Electrochem., 37, 723 (2007); doi:10.1007/s10800-007-9307-3.
S. Ma, J. Liu, S. Li, B. Chen, J. Cheng, J. Kuang, Y. Liu, B. Wan, Y. Wang, J. Ye, Q. Yu, W. Yuan and S. Yu, Adv. Synth. Catal., 353, 1005 (2011); doi:10.1002/adsc.201100033.
M.C. Li, D.D. Bao and C.A. Ma, Electrochim. Acta, 56, 4100 (2011); doi:10.1016/j.electacta.2011.01.115.
J.T. Li, S.R. Chen, X.Y. Fan, L. Huang and S.G. Sun, Langmuir, 23, 13174 (2007); doi:10.1021/la701168x.
J.J. Lu, J.Q. Ma, J.M. Yi, Z.L. Shen, Y.J. Zhong, C.A. Ma and M.C. Li, Electrochim. Acta, 130, 412 (2014); doi:10.1016/j.electacta.2014.03.028.
T. Kurosaki, K.W. Lee and M. Okawara, J. Polym. Sci. A Polym. Chem., 10, 3295 (1972); doi:10.1002/pol.1972.170101116.
T. Endo, K. Takuma, T. Takata and C. Hirose, Macromolecules, 26, 3227 (1993); doi:10.1021/ma00064a039.
D.M. Meier, A. Urakawa and A. Baiker, J. Phys. Chem. C, 113, 21849 (2009); doi:10.1021/jp908071m.
C. Keresszegi, D. Ferri, T. Mallat and A. Baiker, J. Phys. Chem. B, 109, 958 (2005); doi:10.1021/jp0459864.
I.S. Pieta, M. Ishaq, R.P.K. Wells and J.A. Anderson, Appl. Catal. A, 390, 127 (2010); doi:10.1016/j.apcata.2010.10.001.
S. Cinta, C. Morari, E. Vogel, D. Maniu, M. Aluas, T. Iliescu, O. Cozar and W. Kiefer, Vib. Spectrosc., 19, 329 (1999); doi:10.1016/S0924-2031(99)00019-3.
X.H. Guan, G.H. Chen and C. Shang, J. Environ. Sci. (China), 19, 438 (2007); doi:10.1016/S1001-0742(07)60073-4.