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 ( I I b ) 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 ( I I a ) w a s 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 ( V I I I ) in these oxidations w a s confirmed by isolation of nitrosoamides on addition of arnines to the oxidation media.A VARIETY of reagents have been used to oxidise nitrone~,l-~ and such reactions have been reviewed.6-8 Lamchen reported that oxidation of l-pyrroline l-oxides, unsubstituted at the 2-position, with iron (111) chloride gave l-hydroxy-2-pyrrolidones.Oxidation of the same compounds with sodium periodate has indicated that oxidative cleavage to the nitroso-acid proceeds by way of the same hydroxamic acid. The following scheme has been proposed for the reaction :
Die Oxidation des Pyrrolinoxids (III) mit dem Acetat (II) führt zum Pyrrolidon (I) (Ausbeute 64%), mit dem Permanganat (IV) zu den Pentansäuren (VI) und (VII) und dem Pyrolidon (V).
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