How radical cations react? - Distonic radical cation mediated α(nucleophilic), β(radical)-dibenzoloxylation of donor ArCH = CHR

被引：0
作者：
Y. Zhao
W. Li
Q.-Y. Chen
C.-X. Zhao
机构：
[1] Shanghai Jiaotong University,Department of Chemistry
[2] Shanghai Institute of Organic Chemistry,Laboratory of Organo
来源：
Research on Chemical Intermediates | 2001年 / 27卷
关键词：
Oxidation; Physical Chemistry; Peroxide; Inorganic Chemistry; Radical Cation;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Rate determination and product studies have disclosed that the fragmentation pattern of radical cations 2-propenyl-1,4-dimethoxybenzene (1+ ·) and 2-propenyl-1,4,5-trimethoxybenzene (2+·) generated in one-electron oxidation of their parent substrates by 4-nitrobenzoyl peroxide (3) in CH3CN is greatly affected by ring-substitution status of the donor molecules. While ringbenzoloxylation (product 5) predominated in the reaction of dimethoxylated substrate (1), the oxidation of trimethoxylated donor 2 ended up with distonic radical cation mediated α,β-di-4-nitrobenzoloxylation as the major pathway.
引用
收藏
页码：287 / 296
页数：9
相关论文
共 51 条
[1]  
Albini A.(1994)undefined Tetrahedron 50 575-undefined
[2]  
Mella M.(1997)undefined Angrew. Chem. Int. Ed. Engl. 36 2550-undefined
[3]  
Freccero M.(1993)undefined J. Am. Chem. Soc. 115 6426-undefined
[4]  
Schmittel M.(1990)undefined Acta Chem. Scand. 44 645-undefined
[5]  
Burghart A.(1998)undefined Chem. Soc. Rev. 27 81-undefined
[6]  
Evans D. A.(1991)undefined J. Org. Chem. 56 6240-undefined
[7]  
Dinsmore C. J.(1991)undefined J. Am. Chem. Soc. 113 7372-undefined
[8]  
Evrard D. A.(1999)undefined Acc. Chem. Res. 32 815-undefined
[9]  
Devries K. M.(1993)undefined J. Am. Chem. Soc. 115 6564-undefined
[10]  
Baciocchi E.(1982)undefined Tetrahedron 38 1105-undefined
123456