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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
Author(s) -
Bietti Massimo,
Cuppoletti Andrea,
Dagostin Claudio,
Florea Cristina,
Galli Carlo,
Gentili Patrizia,
Petride Horia,
Caia Claudia Russo
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2425::aid-ejoc2425>3.0.co;2-m
Subject(s) - chemistry , deprotonation , alkylation , hydrogen atom , electron transfer , stereochemistry , mechanism (biology) , medicinal chemistry , computational chemistry , photochemistry , organic chemistry , catalysis , ion , group (periodic table) , philosophy , epistemology
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.