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

Abstract

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 N₂O 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 PhCHNR and R′OH.