✦ LIBER ✦

Stereoelectronic Inhibition of Deprotonation in the Radical Cation of N-Benzylpiperidine: a Contribution to the Debate on the Mechanism of N-Dealkylation of Tertiary Amines

✍ Scribed by Massimo Bietti; Andrea Cuppoletti; Claudio Dagostin; Cristina Florea; Carlo Galli; Patrizia Gentili; Horia Petride; Claudia Russo Caia

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 147 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199811)1998:11<2425::aid-ejoc2425>3.0.co;2-m

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✦ Synopsis

Evidence for a stereoelectronic inhibition of deprotonation of versus electron-transfer routes in the biomimetic oxidative N-dealkylation of tertiary amines: the electron-transfer route the radical cation of N-benzylpiperidine is presented. This stereoelectronic effect, which is due to the cyclic structure of appears to be the operating mechanism. the precursor, provides a tool to differentiate hydrogen-atom-