The Reduction of Oximes with Diborane. A New Synthesis of N-Monosubstituted Hydroxylamines

Synthesis of Hydroxylamines

“…Reported yields are highly variable 193,194 although the low yields should be attributed to non-optimal workup procedures rather than to low chemoselectivity. Other borane complexes also reduce oximes in good yield.…”

ChemInform Abstract: New NO Donors with Antithrombotic and Vasodilating Activities. Part 29. N‐(1‐Cyanocyclohexyl)‐C‐phenylnitrones and Glyoxaldinitrones

“…The reaction with different aldehydes leads to the desired nitrones 4. Glyoxaldinitrones (7) were prepared from the corresponding hydroxylamines (6) which in general were obtained by the reduction of oximes (5) with diborane [8] (which was obtained by the method of Hach [9] ).…”

O2‐Mediated Oxidation of Aminoboranes through 1,2‐N Migration

“…[5] Commonly,they are prepared through radical one-step addition of DBPO to the corresponding amine. [7] Orthogonal approaches are based on the reduction of either nitro [8] or oxime [9] moieties to generate primary hydroxylamines.T he direct reductive alkylation of aliphatic nitro compounds via nitroso intermediates remains challenging. [7] Orthogonal approaches are based on the reduction of either nitro [8] or oxime [9] moieties to generate primary hydroxylamines.T he direct reductive alkylation of aliphatic nitro compounds via nitroso intermediates remains challenging.…”