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

…, HV Patel, FF Wong, DN Horng, BR Liaw…

Index: Hwu, Jih Ru; Tseng, Wen Nan; Patel, Himatkumar V.; Wong, Fong Fuh; Horng, Den-Nan; Liaw, Ben Ruey; Lung Ching, Lin Journal of Organic Chemistry, 1999 , vol. 64, # 7 p. 2211 - 2218

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Citation Number: 38

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 ...