One-electron oxidation of alkyl alkoxybenzenes by ω-fluorosulfonylperfluorodiacyl peroxide

被引:3
作者
Dong, JH [1 ]
Dou, HY [1 ]
Zhao, CX [1 ]
机构
[1] Shanghai Jiao Tong Univ, Coll Chem & Chem Engn, Shanghai 200240, Peoples R China
关键词
one-electron oxidation; alkyl alkoxybenzene; omega-fluorosulfonylperfluorodiacyl peroxide; ESR; electron transfer;
D O I
10.1016/j.jfluchem.2005.11.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The oxidation of p-methylanisole 3a, dialkoxybenzenes 3b, 3c and alkyl dialkoxybenzenes 3d-h by perfluorodi[1-(2-fluorosulfonyl) ethoxy]propionyl peroxide 1 afforded main products 4-omega-fluorosulfonylperfluoroalkyl-4-alkoxy-2,5-cyclohexa-dienones and minor ring omega-fluorosulfonylperfluoroalkylation products. The electron transfer mechanism of the reactions is also proved by ESR detection of the radical cations of the donor molecules. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:205 / 212
页数:8
相关论文
共 18 条
[1]   DIACYL PEROXIDE REACTIONS .2. THE REACTION OF DELTA-PHENYLVALERYL PEROXIDE WITH CARBON TETRACHLORIDE [J].
DETAR, DLF ;
WEIS, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (12) :3041-3044
[2]   Synthesis of β-cyclopropylalanines by photolysis of diacyl peroxides [J].
Jain, RP ;
Vederas, JC .
ORGANIC LETTERS, 2003, 5 (24) :4669-4672
[3]  
JENKINS CL, 1971, J ORG CHEM, V36, P3053
[4]   REACTIVITY AND REACTION PATTERNS OF ALKYL ALKOXYBENZENE RADICAL CATIONS - MECHANISTIC PATHWAYS OF THE REACTIONS BETWEEN 2,5-DI-TERT-BUTYL-1,4-DIMETHOXYBENZENE AND PERFLUORODIACYL PEROXIDES [J].
JIANG, XK ;
ZHAO, CX ;
GONG, YF .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1991, 4 (01) :1-6
[5]   THE INTERACTION OF DIACYL PEROXIDES WITH DIAZOMETHANE [J].
LEFFLER, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (10) :4817-4818
[6]   SEPARATION OF DITERPENOID ALKALOID MIXTURES USING VACUUM LIQUID-CHROMATOGRAPHY [J].
PELLETIER, SW ;
CHOKSHI, HP ;
DESAI, HK .
JOURNAL OF NATURAL PRODUCTS, 1986, 49 (05) :892-900
[7]   Chemistry of fluoroalkanoyl peroxides, 1980-1998 [J].
Sawada, H .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 105 (02) :219-220
[8]   Fluorinated peroxides [J].
Sawada, H .
CHEMICAL REVIEWS, 1996, 96 (05) :1779-1808
[9]   Novel self-assembled molecular aggregates formed by fluoroalkyl end-capped oligomers and their application [J].
Sawada, H .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 121 (02) :111-130
[10]   Architecture and applications of novel self-assembled aggregates of fluoroalkyl-end-capped oligomers [J].
Sawada, H .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 101 (02) :315-324