Water-controlled nitro-oximation of alkenes under catalyst-free conditions.

Graphical abstract Highlights • No use of any catalyst. • No external oxidant and additive. • Reaction in aqueous media. • Gram-scale synthesis. Abstract A convenient and precise nitration and oximation of alkenes with tert -butyl nitrite has been reported, yielding α-nitro ketoximes in satisfactory yields with broad substrate generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert -butyl nitrite serves as both NO and NO 2 sources and water plays a key role in this difunctionalization reaction. [ABSTRACT FROM AUTHOR]