Tetrahedron letters

Copper-induced synthesis of iminiums: trimethylamine oxidation or amine N-oxide conversion

G Rousselet, M Maumy

Index: Rousselet, Guilhem; Capdevielle, Patrice; Maumy, Michel Tetrahedron Letters, 1995 , vol. 36, # 28 p. 4999 - 5002

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Citation Number: 26

Abstract

The ClCuIIOCuIICl reagent as well as the O 2Cu IOAc system oxidize trimethylamine 1a into N, N-dimethyliminium 3a, characterized by its phenolic adduct 5a. This reaction appears to be a biomimetic model for laccase or human ceruloplasmin activity towards tertiary amines. Amine N-oxides react with CuI or CuII salts to give iminiums 3a-c, likewise trapped in good yields.