Studies on lead tetraacetate oxidation of α-oxoketene dithioacetals

Article abstract of DOI:10.1016/S0040-4020(01)80925-X

Lead Tetraacetate oxidation of acyclic α-acylketene dithioacetals 1 in refluxing benzene affords α-acetoxyketene dithioacetals 2 as major products which could be hydrolyzed to α-diketone dithioacetals 4 under mild alkaline conditions. Under similar oxidative conditions, α-cinnamoyl ketene dithioacetals 8 yield 2-acetoxycyclopentenone derivatives 9 through an interesting oxidative Nazarov cyclization involving intermediate α-acetoxy dithioacetals accompanied with 1,2-acyl group migration.