Journal of the American Chemical Society p. 7358 - 7367 (1988)
Update date:2022-08-16
Topics:
Seok, Won K.
Meyer, Thomas J.
The kinetics of oxidation of phenol and alkylated phenol derivatives by <(bpy)2(py)Ru(IV)(O)> (2+) and <(bpy)2(py)Ru(III)(OH)>(2+) (bpy is 2,2'-bipyridine and py is pyridine) to give the corresponding quinones have been studied in aqueous solution and in acetonitrile.The reactions are first order in both phenol and Ru(IV)=O(2+) or Ru(III)-OH(2+).They proceed via a detectable intermediate, which is a Ru(II) complex. 18O isotopic labeling experiments show that transfer of the oxo group from Ru(IV)=O(2+) to phenol is quantitative.The reactions are facile.With Ru(IV)=O(2+) as oxidant k(25 deg C, CH3CN) = 1.9 (+/-0.4) E2M-1s-1; with Ru(III)-OH(2+) as oxidant k(25 deg C, CH3CN) = 4.0 (+/-0.4) E1M-1s-1.On the basis of the rate laws, the magnitude of OH/OD and CH/CD kinetic isotope effects, and the 18O labeling results, the most reasonable mechanisms for oxidation of phenol by Ru(IV)=O(2+) appears to be electrophilic attack on the aromatic ring.For Ru(III)-OH(2+), oxidation appears to occur by CH/H atom transfer in CH3CN and OH/H atom transfer in water.
View MoreContact:+86-512-56795332
Address:No227 Shuanglong Rd, Fenghuang, Zhangjiagang
Luzhou North Chemical Co., Ltd.
Contact:+86-830-2796784;+86-830-2796776
Address:Gaoba, Longmatan District, Luzhou, Sichuan Province
Shanghai Forever Synthesis Co.,Ltd.
Contact:021-61124658
Address:Zhoukang Road,Pudong New District,Shanghai,China
Shanghai Yingrui Biopharma Co., Ltd
Contact:021-3358 8661*8003
Address:shanghai
Shandong Jusage Technology Co.,Ltd.
Contact:86-13406130167
Address:No.20,North Ride No.9 Road, Guangrao Economic Development Zone, Shandong Province
Doi:10.1002/ejic.201500010
(2015)Doi:10.1039/b612975g
(2007)Doi:10.1021/j100154a032
(1991)Doi:10.1080/00397919208021602
(1992)Doi:10.1016/j.polymer.2015.09.050
(2015)Doi:10.1021/jo401799f
(2013)