Aerobic Metal-Free Dioxygenation of Alkenes with <i>tert</i>-Butyl Nitrite and <i>N</i>‑Hydroxylamines

Metal-free dioxygenation of alkenes with <i>tert</i>-butyl nitrite and <i>N</i>-hydroxylamines (<i>N</i>-hydroxyphthalimide, <i>N</i>-hydroxybenzotriazole, and <i>N</i>-hydroxysuccinimide) is described to produce β-aminoxy nitrate esters using air as the oxidant. These organic nitrates can be readily converted into 1,2-diols and 1,2-diketone with broad substrate scope and functional group diversity