Unexpected Formation of Benzaldehydes by the Reactions of Dithio- Acetals Derived from Cinnamaldehydes with 2,3-Dichloro-5,6-dicyano-p-benzoquinone in Aqueous Solvents

Article abstract of DOI:10.1002/jhet.5570340216

1,3-Dithianes 1, 1,3-dithiolanes 2, and diphenyl dithioacetals 3 derived from cinnamaldehydes reacted with 2,3-dichloro-5,6-dicyano-p-benzoquinone in aqueous solvents to give benzaldebydes 4. Hydride transfer from 1-3 to 2,3-dichloro-5,6-dicyano-p-benzoquinone followed by hydrolysis and oxidative carbon-carbon bond cleavage would produce benzaldehydes 4.