title: 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 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.
authors.affiliation: Drug Design Section, Chemical Biology Laboratory, National Cancer Institute at Frederick, Frederick, MD 21702, USA. biswasd@mail.nih.gov
authors.forename: Debanjan
authors.initials: D
authors.lastname: Biswas
authors.forename: Zhao
authors.initials: Z
authors.lastname: Cao
authors.forename: Larry K
authors.initials: LK
authors.lastname: Keefer
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Saavedra
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D001596:Benzylamines / Q000737:chemistry*; D009609:Nitrous Oxide / Q000737:chemistry*; D011355:Prodrugs
chemical_list: D001391:Azo Compounds; D001596:Benzylamines; D011355:Prodrugs; D009609:Nitrous Oxide