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

Stereoelectronic inhibition of deprotonation in the radical cation of N-benzyl piperidine: a contribution to the debate on the mechanism of N-dealkylation of tertiary amines / M., Bietti; A., Cuppoletti; C., Dagostin; C., Florea; Galli, Carlo; Gentili, Patrizia; H., Petride; C., RUSSO CAIA. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (1998), pp. 2425-2429. [10.1002/(SICI)1099-0690(199811)1998:11<2425::AID-EJOC2425>3.0.CO]

Stereoelectronic inhibition of deprotonation in the radical cation of N-benzyl piperidine: a contribution to the debate on the mechanism of N-dealkylation of tertiary amines

GALLI, Carlo;GENTILI, Patrizia;
1998

Abstract

Evidence for a stereoelectronic inhibition of deprotonation of the radical cation of N-benzylpiperidine is presented. This stereoelectronic effect, which is due to the cyclic structure of the precursor, provides a tool to differentiate hydrogen-atom-versus electron-transfer routes in the biomimetic oxidative N-dealkylation of tertiary amines: the electron-transfer route appears to be the operating mechanism.
1998
01 Pubblicazione su rivista::01a Articolo in rivista
Stereoelectronic inhibition of deprotonation in the radical cation of N-benzyl piperidine: a contribution to the debate on the mechanism of N-dealkylation of tertiary amines / M., Bietti; A., Cuppoletti; C., Dagostin; C., Florea; Galli, Carlo; Gentili, Patrizia; H., Petride; C., RUSSO CAIA. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - (1998), pp. 2425-2429. [10.1002/(SICI)1099-0690(199811)1998:11<2425::AID-EJOC2425>3.0.CO]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/253722
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