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OPENING OF THE FURAN RING OF 3-NITROBENZOFURANS BY THE ACTION OF CARBONYL-STABILIZED SULFONIUM YLIDES

Ирина А. Семенова, Виталий А. Осянин, Олег П. Демидов, Дмитрий В. Осипов
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Abstract


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.

Keywords


dimethylphenacylsulfonium salts; 3-nitrobenzofurans; sulfur ylides; Michael reaction; nucleophilic dearomatization.

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