Mono-deoxygenation of Nitroalkanes, Nitrones, and Heterocyclic N -Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”
1999; American Chemical Society; Volume: 64; Issue: 7 Linguagem: Inglês
10.1021/jo981054i
ISSN1520-6904
AutoresJih Ru Hwu, Wen Nan Tseng, Himatkumar V. Patel, Fong Fuh Wong, Den‐Nan Horng, Ben Ruey Liaw, Lung Ching Lin,
Tópico(s)Chemical Synthesis and Analysis
ResumoTransformation 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.
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