Nitrous oxide as a primary product in base-mediated β-elimination reactions of diazeniumdiolated benzylamine derivatives

We report an unexpected β-elimination pathway by which diazeniumdiolated benzylamines of structure Bn-N(R)-N(O)=N-OR' undergo base-mediated fragmentation to generate N(2)O as the only gaseous product. The reaction is especially rapid for R = 2-hydroxyethyl, in which the hydroxyl group anchimerically assists benzylic proton removal with concomitant expulsion of PhCH=NR and R'OH.