Tetrahedron letters

Highly efficient and mild synthesis of nitrones by catalytic oxidation of hydroxylamines with tetra-n-propylammonium perruthenate

A Goti, F De Sarlo, M Romani

Index: Goti, Andrea; De Sarlo, Francesco; Romani, Michela Tetrahedron Letters, 1994 , vol. 35, # 35 p. 6571 - 6574

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Citation Number: 61

Abstract

Abstract Oxidation of N, N-disubstituted hydroxylamines by N-methylmorpholine N-oxide (NMO) and catalytic amounts of tetra-n-propylammonium perruthenate (TPAP) at room temperature occurs very rapidly to give the corresponding nitrones, which can be trapped by dipolarophiles present in the reaction mixture, in excellent yields. A competitive experiment in the presence of a primary alcohol gave a> 50: 1 nitrone to aldehyde ratio.