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Oxidative dealkylation of a hindered phenol catalyzed by copper (II) bis benzimidazole diamide complex |
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| Authors: | Manisha Gupta M.A. Sridhar |
| Affiliation: | a Acharya Narendra Dev College, University of Delhi, Delhi 110007, India b Department of Chemistry, University of Delhi, Delhi 110007, India c Department of Physics, University of Mysore, India |
| Abstract: | The oxidative dealkylation of 2,4,6-tri-tert-butylphenol (TTBP) has been investigated using molecular oxygen and [Cu(NO3(GBHA)](NO3) as catalyst, where GBHA is N,N′-bis((benzimidazol-2-yl)methyl)hexanediamide [(a) M. Gupta, P. Mathur, R.J. Butcher, Inorg. Chem. 40 (2001) 878; (b) M. Gupta, S.K. Das, P. Mathur, A.W. Cordes, Inorg. Chim. Acta 353 (2003) 197; (c) S. Tehlan, M.S. Hundal, P. Mathur, Inorg. Chem. 43 (2004) 6589; (d) F. Afreen, P. Mathur, A. Rheingold, Inorg. Chim. Acta 358 (2005) 1125.]. X-ray structural characterization of complex [Cu(NO3)(GBHA)](NO3) · CH3OH confirms that the Cu (II) ion is in a distorted square pyramidal geometry (τ = 0.168). The TTBP oxidation reaction proceeds via tri-tert-butylphenoxyl radical producing two products 2,6-di-tert-butyl-1,4-benzoquinone (A) and 4,6-di-tert-butyl-1,2-benzoquinone (B). Both A and B have been well characterized by 1H NMR, 13C NMR, UV-Vis and mass data. |
| Keywords: | Benzimidazole diamides Copper(II)-Metalloproteins Tri-tert-butylphenol Oxidative dealkylation |
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