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Abstract | Cited by

We report an unexpected β-elimination pathway by which diazeniumdiolated benzylamines of structure Bn–N(R)–N(O)[double bond, length as m-dash]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 PhCH[double bond, length as m-dash]NR and R′OH.

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

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