Oxidation of a 1-pyrroline 1-oxide and the corresponding 1-hydroxy-2-pyrrolidone

Abstract

The oxidation of 4,5,5-trimethyl-1-pyrroline 1-oxide (I) with lead tetra-acetate gives 1-acetoxy-4,5,5-trimethyl-2-pyrrolidone (IIb) in 64% yield; with an excess of potassium permanganate the major product was 3,4-dimethyl-4-nitropentanoic acid (IVa). 1-Hydroxy-4,5,5-trimethyl-2-pyrrolidone (IIa) was cleaved upon treatment with potassium permanganate or lead tetra-acetate and gave novel compounds derived from two molecules of (IIa). The existence of a nitroso-acylating species (VIII) in these oxidations was confirmed by isolation of nitrosoamides on addition of amines to the oxidation media.