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

• Authors: Horia Petride , Constantin Drãghici , Cristina Florea , Aurica Petride
• Languages of publication: EN

Abstracts

EN

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

EN

oxidation; ruthenium tetraoxide; amines; iminium cations; regioselectivity

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2004
• Volume: 2
• Issue: 2
• Pages: 302-322

Dates

published

1 - 6 - 2004

online

1 - 6 - 2004

Contributors

author

Horia Petride

• Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania

author

Constantin Drãghici

• Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania

author

Cristina Florea

• Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania

author

Aurica Petride

• Centrul de Chimie Organicã “Costin D. Nenitzescu”, 060111 15-254, Bucuresti, Romania

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Identifiers

DOI

10.2478/BF02475575