Thermal isomerization of cis- and trans-dimethyl epoxymethylsuccinate to dimethyl α-oxoglutarate

Abstract

An unusual rearrangement of the methyl substituted epoxides, cis- and trans-dimethyl epoxymethylsuccinate, to the straight-chain ketone, dimethyl α-oxo-glutarate, is described together with the patially analogous rearrangements of the cis- and trans-dimethyl 1-methylcyclopropane-1,2-dicarboxylates into dimethyl α-methyleneglutarate and cis- and trans-dimethyl 1,2-dimethylaziridine-2,3-dicarboxylates into methyl 1-methoxycarbonyl(methyl)acrylate.