A straightforward oxidation of dienones to 2-acetylfurans by selenium dioxide
Z No, YB Chae, CJ Shin, Y Chung
Index: No, Zaesung; Chae, Yung Bog; Shin, Chan Jae; Chung, Yongseog Tetrahedron Letters, 1998 , vol. 39, # 34 p. 6191 - 6194
Full Text: HTML
Citation Number: 7
Abstract
Direct oxidation of (E)-4-(6-substituted-1-cyclohexenyl)-3-buten-2-ones (4a–7a) by selenium dioxide afforded 2-acetyltetrahydrobenzofurans (4b–7b) in moderate to good yields. An inverse, stepwise [2+ 4] cycloaddition mechanism of the intermediate formation was proposed from conformational and electronic requirements of conjugated dienones and solvent effects of SeO2 oxidation.
Related Articles:
13C NMR of carbonyl compounds-4. Solution conformation of β-ionone and related dienones
[Muellen, K.; Schmickler, H.; Frei, B.; Wolf, H. R. Tetrahedron Letters, 1986 , vol. 27, # 4 p. 477 - 480]