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Volume 1 (2003)

RuO4-mediated oxidation ofN-benzylated tertiary amines. Are amineN-oxides and iminium cations reaction intermediates?

Horia Petride / Constantin Drãghici / Cristina Florea / Aurica Petride
Published Online: 2004-06-01 | DOI: https://doi.org/10.2478/BF02475575

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Abstract

N-Benzylmorpholine,-piperidine, and-pyrrolidine (1A-C, resp.) are oxidised by RuO4 (generatedin situ) at both endocyclic and exocyclic (benzylic)N—α-methylene positions to afford lactams (and dioxo-derivatives) and benzaldehyde (and benzoyl derivatives), respectively. TheN-oxides of1A-C, formed by a minor side reaction, are not involved as intermediates. Control experiments showed the transient formation of endo- and exocyclic iminium cations trapped with NaCN as the corresponding nitriles. The proposed course of the RuO4-mediated oxidation of1A-C involves the consecutive steps1⇒iminium cations+cyclic enamine⇒oxidation products. The endocyclic/exocyclic regioselectivity of the oxidation reaction lies between 0.8 (for1A) and 2.1 (for1B). The amine cation radical and theN-α-C· carbon-centered radical seem not to be involved.

Keywords: oxidation; ruthenium tetraoxide; amines; iminium cations; regioselectivity

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About the article

Published Online: 2004-06-01

Published in Print: 2004-06-01

Citation Information: Open Chemistry, Volume 2, Issue 2, Pages 302–322, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/BF02475575.

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