Direct C-nitration of cyclic α,β-unsaturated oximes under the action of sodium nitrite and acetic acid in methanol

Abstract

Using a number of cyclic α,β-unsaturated oximes of the terpene series and some simplest model compounds as examples, unsaturated oximes bearing a hydrogen atom at the β-carbon atom were demonstrated to be converted into β-hydroxyiminonitroalkenes under the action of sodium nitrite and acetic acid in methanol. In the case of the introduction of an alkyl substituent at the terminal carbon atom of the diene C=C—C=NOH fragment, the reaction performed under the same conditions gave rise exclusively to conjugated ketone (a deoximation product).