1378023-64-3Relevant academic research and scientific papers
Nitrous oxide as a primary product in base-mediated β-elimination reactions of diazeniumdiolated benzylamine derivatives
Biswas, Debanjan,Cao, Zhao,Keefer, Larry K.,Saavedra, Joseph E.
, p. 5931 - 5933 (2012)
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.
