Affordable Access

Iron(II, III)-catalyzed oxidativeN-dealkylation of amines with dioxygen

Authors
Journal
Journal of Molecular Catalysis A Chemical
1381-1169
Publisher
Elsevier
Publication Date
Volume
212
Identifiers
DOI: 10.1016/j.molcata.2003.11.018
Keywords
  • N-Demethylation
  • N-Dealkylation
  • Dioxygen Activation
  • Alkylated Amines
  • Iron Complexes

Abstract

Abstract Labile iron complexes (e.g., [Fe III(bpy) 2] MeCN 3+, [Fe II(bpy) 2] MeCN 2+, [Fe III(H 2O) 6] MeCN 3+, and [Fe II(H 2O) 6] MeCN 2+) in base-free acetonitrile activate dioxygen for the direct oxygenation of N,N- and N-alkylated amines to form N-dealkylated products and corresponding aldehydes. N,N-dimethylaniline (DMA) is oxidized to N-methylaniline (MA) and formaldehyde as well as to N-methylanilide. Formaldehyde and the excess of substrate undergo condensation reaction to produce 4,4′-methylenebis( N,N-dimethylaniline) (MBDME). Small amounts of N-methylformanilide (MF) and formanilide are also formed during oxidation of N,N-dimethylaniline and N-methylaniline respectively. Iron(III) catalysts are reduced by the substrate to iron(II), which activates dioxygen. Dioxygen activation step is preceded by the equilibrium reaction between iron(II) catalyst and substrate.

There are no comments yet on this publication. Be the first to share your thoughts.

Statistics

Seen <100 times
0 Comments

More articles like this

OxidativeN-dealkylation of triethylamine by molecu...

on Journal of Molecular Catalysis Jan 01, 1986

Oxidative dealkylation of tertiary amines by iron(...

on CHEMICAL & PHARMACEUTICAL BULL... May 1981

Factors affecting cytochrome P-450 and horseradish...

on Journal of Molecular Catalysis Jan 01, 1993
More articles like this..