Diethyl chlorophosphite: a versatile reagent.

Diethyl chlorophosphite (DECP) was previously described as a reducing agent for nitro compounds to the corresponding amines (Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393). Here, the utility of this reagent was extended to chemical conversions of other oxygenated functional groups. In this paper we report on the scope of the reaction of DECP with N-oxides, epoxides, sulfones, sulfoxides, hydroxylamines, ketoximes, and aldoximes. The chemoselectivity of DECP is described, and conditions for a stepwise multiple conversion of functional groups on the same molecule with this reagent are provided.