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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.

SUBMITTER: Biswas D

PROVIDER: S-EPMC6959517 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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

Biswas Debanjan D Cao Zhao Z Keefer Larry K LK Saavedra Joseph E JE

Chemical communications (Cambridge, England) 20120509 47

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. ...[more]

PMID: 22572739

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