Counterattack reagents: Thiosilanes in the conversion of nitro compounds to thiohydroxamic acids and thiohydroximates
作者:Jih Ru Hwu、Shwu-Chen Tsay
DOI:10.1016/s0040-4020(01)89057-8
日期:——
Mono-deoxygenation of Nitroalkanes, Nitrones, and Heterocyclic <i>N</i>-Oxides by Hexamethyldisilane through 1,2-Elimination: Concept of “Counterattack Reagent”
作者:Jih Ru Hwu、Wen Nan Tseng、Himatkumar V. Patel、Fong Fuh Wong、Den-Nan Horng、Ben Ruey Liaw、Lung Ching Lin
DOI:10.1021/jo981054i
日期:1999.4.1
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.