Recueil des Travaux Chimiques des Pays-Bas p. 52 - 62 (1988)
Update date:2022-08-16
Topics:
Eijk, Peter J. S. S. van
Trompenaars, Willem P.
Reinhoudt, David N.
Harkema, Sybolt
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.
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