ALPHA-KETO AMIDES AND 1,2-DIKETONES FROM N,N'-DIMETHOXY-N,N'-DIMETHYLETHANEDIAMIDE - A SYNTHETIC AND MECHANISTIC INVESTIGATION

N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl syntho n prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide alpha-keto amides 2-12 in 28-90% yie lds. The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84% yields. A mechanism accounting for all the products from the re action of 1 with nucleophiles has been proposed. Several control exper iments were carried out to support the proposed mechanism.