Mono-deoxygenation of Nitroalkanes, Nitrones, and Heterocyclic<i>N</i>-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”

Abstract

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.