Nitrous oxide as a primary product in base-mediated β-elimination reactions of diazeniumdiolated benzylamine derivativesElectronic supplementary information (ESI) available: Full experimental procedures and spectroscopic data for compounds 3, 4, 7a, 7b, and 9 are available. See DOI: 10.1039/c2cc32284f

We report an unexpected β-elimination pathway by which diazeniumdiolated benzylamines of structure Bn-N(R)-N(O)&z.dbd;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 anch...

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Bibliographic Details
Main Authors: Biswas, Debanjan, Cao, Zhao, Keefer, Larry K, Saavedra, Joseph E
Format: Article
Language:English
Online Access:Get full text
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Summary:We report an unexpected β-elimination pathway by which diazeniumdiolated benzylamines of structure Bn-N(R)-N(O)&z.dbd;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&z.dbd;NR and R′OH. Diazeniumdiolated benzylamines of structure Bn-N(R)-N(O)&z.dbd;N-OR′ undergo base-mediated β-elimination reactions to generate N 2 O, PhCH&z.dbd;NR and R′OH.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc32284f