Reactions of Aliphatic Imides with Oxalyl Chloride

Article abstract of DOI:10.1021/jo00328a004

Simple aliphatic acid imides like diacetamide (1a), dipropionamide (1b), and diisobutyramide (6) react with oxalyl chloride with formation of O-acylated products of type 2a,b and 7, the structure of which was assigned on the basis of 1H-NMR and 13C-NMR data.Thermolysis of 2a,b results in HCl abstraction and ring closure, giving oxazolidinediones 5a,b.Heat treatment of 7 yields isobutyryl chloride and isobutyryl isocyanate.Glutarimide (10a) and adipimide (10b) yield fused heterocycles of type 12 directly when treated with oxalyl chloride.