Aliphatic nitro compounds chemistry: oximes–nitrones tunable production through directed tandem synthesis

Abstract

Reduction of aliphatic nitro compounds in the presence of aldehydes and dialdehydes for tunable directed synthesis of oximes, nitrones, nitrone–oximes, and dinitrones was reported. The slow and nonselective reduction of aliphatic nitro compounds was directed by condensation of in situ prepared alkylhydroxylamines with aromatic aldehydes. Mononitrones and dinitrones were synthesized at reflux and at 55 °C conditions, respectively, in tetrahydrofuran using SnCl2·2H2O and Na2CO3. It was found that the presence of a catalytic amount of carboxylic acid such as 3-phenylpropanoic acid increases the yield of dinitrones versus nitrone–oxime and dioxime when dialdehydes were used as aldehyde source.