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A straightforward oxidation of dienones to 2-acetylfurans by selenium dioxide

✍ Scribed by Zaesung No; Yung Bog Chae; Chan Jae Shin; Yongseog Chung

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
217 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Direct oxidation of (E)-4-(6-substituted-l-cy. clohexenyl)-3-bulen-2-ones (4a,,-7a) by selenium dioxide afforded 2-acetyltetrahydrobenzofurans (4b~Tb) in moderate to good yields. An inverse, stepwise [2+4] cycloaddilion mechanism of the intermediate formation was proposed from conformational and electronic requirements of conjugated dienones and solvent effects of SeO2 oxidation.

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