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Radical cations of 1,4-dialkoxybenzenes and alkyl 1,4-dialkoxybenzenes generated through one-electron oxidation by perfluorodiacyl peroxides
Authors:Jun-Hua Dong  Hong-Yan Dou  Yue-Fa Gong  Cheng-Xue Zhao
Institution:(1) Department of Chemistry, University of Florida, Box 117200, Gainesville, FL 32611-7200, USA;(2) Division of Nephrology, Hypertension and Renal Transplantation, Department of Medicine, University of Florida, Box 100224, Gainesville, FL 32610, USA;(3) Division of Renal Diseases and Hypertension, University of Colorado Health Science Center, Box C-281, 4200 E 9th Ave, Denver, CO 80262, USA;
Abstract:Radical cations of 1,4-dialkoxybenzenes 1 and 2 and alkyl 1,4-dialkoxybenzenes 3–9 generated in oxidation of the parent donors by perfluorodi1-(2-fluorosulfonyl)ethoxy]propionyl peroxide 10 at −40°C and pentafluorobenzoyl peroxide 11 at 15°C were observed by ESR. Radical cation 6, generated in other oxidation systems, i.e., Ce(SO4)2/THF, NH4/OAc and (NH4)2S2O8/HOAc, has also been investigated. Based on ESR observation and products analysis, an electron-transfer mechanism of the oxidation reaction is proposed and the influencing factors on hyperfine splitting constants of the radical cations are discussed.
Keywords:ESR  DIALKOXYBENZENE RADICAL CATIONS  PERFLUORODIACYL PEROXIDE  ONE-ELECTRON OXIDATION
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