The Journal of Organic Chemistry

. alpha.-Keto Amides and 1, 2-Diketones from N, N'-Dimethoxy-N, N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation

MP Sibi, M Marvin, R Sharma

Index: Sibi, Mukund P.; Marvin, Mali; Sharma, Rajiv Journal of Organic Chemistry, 1995 , vol. 60, # 16 p. 5016 - 5023

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Citation Number: 44

Abstract

N,”-Dimethoxy-N,”-dimethylethanediamide (11, a 1, 2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide a- keto amides 2-12 in 28-90% yields. 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 reaction of 1 with ...