Conversion of hydrazones to alkyl chlorides under Swern oxidation conditions

The unsubstituted hydrazones derived from aromatic ketones and aldehydes were converted in high yield to the corresponding alkyl chlorides under Swern oxidation conditions. In this unusual oxidation/reduction sequence the substrate undergoes a net reduction under the well established Swern oxidation conditions. Unsubstituted hydrazones derived from cyclohexyl ketones returned elimination products.