Reaction of four-membered cyclic nitrones with acetyl chloride. X-Ray crystal structures of 2--N,N-diethyl-2-methyl-4-oxo-3-phenylpentanamide and 1-acetyl-3-chloro-N,N-diethyl-2-methyl-4-methylene-3-phenyl-2-azetidinecarboxamide

Article abstract of DOI:10.1002/recl.19881070204

Reactions of the four-membered cyclic nitrones 1 with acetyl chloride differ strongly from those of other (cyclic) nitrones.In the presence of water, the nitrones 1 yield the 2-<(acetyloxy)amino>-N,N-diethylalkanamides 4.The structure of 4b was confirmed by X-ray analysis.In the absence of water, the N,N-diethyl-4-methylene-2-azetidinecarboxamides 5 or the N,N-diethyl-2,3-dihydro-2-azetecarboxamides 6 were obtained.X-ray analysis elucidated the structure of 5a.Under acidic conditions, compound 5a yielded the 2-oxa-5-azabicyclo<2.1.1>hexan-3-one derivative 13.Acid hydrolysis of 6a gave the α-chloroketone derivative 18 and the 2-oxopropanamide derivative 19.