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

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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.

Affiliations: 1: Department of Chemistry, Shanghai Jiaotong University, Shanghai 200240, China; 2: Department of Chemistry, Shanghai Jiaotong University, Shanghai 200240, China; Laboratory of Organo-fluorine Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China; 3: Laboratory of Organo-fluorine Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China

10.1163/156856701300356509
/content/journals/10.1163/156856701300356509
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/content/journals/10.1163/156856701300356509
2001-04-01
2016-12-03

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