Tetrahedron Letters p. 2413 - 2416 (1998)
Update date:2022-08-04
Topics:
Iliefski, Tommy
Li, Shiming
Lundquist, Knut
1-Arylpropenes and 3-arylpropenes give cinnamaldehydes (yield= 80%) on oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in the presence of water. The conversion to aldehydes is promoted by electron-donating groups at the aromatic ring. On DDQ oxidation in the presence of methanol, methyl esters of cinnamic acids are the predominant products. DDQ oxidation of 1- or 3-(3,4-dimethoxyphenyl)-1-propene in the presence of acetic acid gives an acylal [the diacetate of (E)-3-(3,4-dimethoxyphenyl)-2-propene-1, 1-diol].
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