The electrolysis of methyl hydrogen cis-cyclop:opane-l,2-dicarboxylate has been reinvestigated. The products include dimethyl bicyclopropyl-2,2'-dicarboxylates, which arise by radical coupling, and methyl 2-methoxybut-3-enoate, which is formed through a carbonium ion intermediate. Cyclopropanecarboxylic acid has been electrolysed in sulpholan.FICHTER AND SPIEGELBERG reported 2 in 1929 that the Kolbe-coupled product. Saponification of the ester electrolysis of sodium methyl cis-cyclopropane-1,2-di-gave the di-acid, C,HloO,, which on the basis of its carboxylate in methanol and in water in each case gave rapid reaction with alkaline permanganate and the coa low yield of an ester, C10H1404, corresponding to the incidence of its melting point with that of a compound

MeCO-CH (CO,Et).CH (CO,Et).COMe each react w i t h 2.4-dinitrophenylhydrazine to give a mixture of the corresponding N-(2,4-dinitroanilino)pyrrole and the bis-2.4-dinitrophenylhydrazone.IN connection with other studies,l we have investigated the reaction of diethyl crd-diacetylsuccinate (I; R = R' = C0,Et) with 2,4-dinitrophenylhydrazine. This 1,4-diketone has been reported to react with arylhydr-MeCOCHRCHR'COMe (I) azines 2 9 3 to give products which have been formulated either as K-anilinopyrroles or as N-aryldihydropyridazines . 3 The related dike t one ace t on ylacet one (I; R = K' = H) has frequently been characterised as its bi~-2,4-dinitrophenylhydrazone,~" but two mono-2,4-dinitrophenylhydrazones have also been r e p ~r t e d , ~. ~ and it seemed necessary to reinvestigate these also.The pale yellow crystalline solid obtained in high yield from diethyl ad-diacetylsuccinate (I; R = €3' = C0,Et) and Brady's reagent was shown by the analytical data and its infrared spectrum, which showed a band at 3270 cm.-l (NH), to be either diethyl 1-(2,4-dinitro-R = R' = C0,Et) or diethyl 1-(2,4-dinitropheny1)-1,2dihydro-3,B-dime thylpyridazine-4,5-dicarboxylat e (I I I ; R = R' == C0,Et). The . nuclear magnetic resonance (n.m.r.) spectrum of this product showed the equivalence of the two ring-methyl groups and of the two ester-ethyl groups, and hence indicated that the product is the A T -anilino) -2,5-dimethylpyrrole-3,4-dicarboxylate (11;

Anodic Oxidation. Part 1. The Electrolysis of Ethyl Sodioacetoacetate in Ethanolic SystemsBy T. D. Binns and R. Brettle Acetaldehyde is produced when solutions of ethyl sodioacetoacetate in ethanol or aqueous ethanol are electrolysed using a platinum anode and a mercury cathode. Products arising from the condensation of acetaldehyde with ethyl acetoacetate result, and a reinvestigation of these products and of their 2,4-dinitrophenylhydrazones is reported. No diethyl aa'-diacetylsuccinate can be detected amongst the electrolysis products.\VE have reinvestigated the electrolysis of solutions of ethyl sodioacetoacetate. Early workers used 50% aqueous ethanol as the solvent, but initially we performed the electrolysis in absolute ethanol.Electrolysis of Ethyl Sodioacetoacetate in Ethanol.-Methanol has commonly been used as the solvent for anodic oxidations in recent years but ethanol, which has occasionally been used,4 was chosen in this case to eliminate transesterification. The cell was of a conventional type, with a platinum anode. With a platinum cathode it is difficult to follow the progress of the electrolysis, a s the pH of the electrolyte does not change as in a

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