Mono-deoxygenation of nitroalkanes, nitrones, and heterocyclic N-oxides by hexamethyldisilane through 1,2-elimination:: Concept of "counterattack reagent"

Transformation of secondary nitroalkanes to ketoximes was achieved in 40-73% yields by treatment of the corresponding nitronate anions with hexamethyldisilane. In this new mono-deoxygenation process, hexamethyldisilane acted as a "counterattack reagent". The conversion of nitrones to imines was also achieved in 82-88% yields by use of trimethylsilyllithium. Similarly, heterocyclic N-oxides were converted to the corresponding N-heterocycles in 73-86% yields. These deoxygenation processes presumably involve a 1,2-elimination.