Opening of the Furan Ring of 3-Nitrobenzofurans by the Action of Carbonyl-Stabilized Sulfonium ylides

被引：0
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作者：
Irina А. Semenova
Vitaly А. Osyanin
Oleg P. Demidov
Dmitry V. Osipov
机构：
[1] Samara State Technical University,
[2] North Caucasus Federal University,undefined
来源：
Chemistry of Heterocyclic Compounds | 2022年 / 58卷
关键词：
dimethylphenacylsulfonium salts; 3-nitrobenzofurans; sulfur ylides; Michael reaction; nucleophilic dearomatization;
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摘要：
Upon treatment of 3-nitrobenzofurans with dimethylphenacylsulfonium salts in the presence of a base, the opening of the furan ring to form (E)-1-aryl-2-(dimethylsulfonio)-4-nitro-1-oxobut-3-en-2-ides takes place. The mechanism of nucleophilic dearomatization of 3-nitrobenzofurans involves consecutive carbo- and retro-oxa-Michael reactions. The reaction illustrates the high propensity of 3-nitrobenzofurans for ring opening.
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页码：251 / 254
页数：3
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