STEREOELECTRONIC INHIBITION OF DEPROTONATION IN THE RADICAL-CATION OFN-BENZYLPIPERIDINE - A CONTRIBUTION TO THE DEBATE ON THE MECHANISM OFN-DEALKYLATION OF TERTIARY-AMINES

Authors
BIETTI M CUPPOLETTI A DAGOSTIN C FLOREA C GALLI C GENTILI P PETRIDE H CAIA CR
Citation
M. Bietti et al., STEREOELECTRONIC INHIBITION OF DEPROTONATION IN THE RADICAL-CATION OFN-BENZYLPIPERIDINE - A CONTRIBUTION TO THE DEBATE ON THE MECHANISM OFN-DEALKYLATION OF TERTIARY-AMINES, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (11), 1998, pp. 2425-2429
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
11
Year of publication
1998
Pages
2425 - 2429
Database
ISI
SICI code
1434-193X(1998):11<2425:SIODIT>2.0.ZU;2-F
Abstract
Evidence for a stereoelectronic inhibition of deprotonation of the rad ical cation of N-benzylpiperidine is presented. This stereoelectronic effect, which is due to the cyclic structure of the precursor, provide s a tool to differentiate hydrogen-atom-versus electron-transfer route s in the biomimetic oxidative N-dealkylation of tertiary amines: the e lectron-transfer route appears to be the operating mechanism.