β-Chloroamine hydrochlorides, produced stereospecifically and regiospecifically from aziridines with anhydrous hydrogen chloride in ether, are condensed with sodium carbonate in dry DMSO to afford isomerically pure 2-oxazolidinones.
The azirine formation by LAH reduction of oximes has been extended to several types, such asandThe result was satisfactory to generalization of this reaction.
Aziridines I react with trifluoromethylhypofluorite at − 40°C to produce mixtures of 1-(aziridine)carbonylfluoride II and 1-fluoroaziridine III, the proportions of which depend on steric effects. Several compounds II react with starting materials to give 1, 1′-(carbonyl)bisaziridines IV. Most compounds II and all compounds IV are isolated. Chemical properties and ir and nmr data of II, III, IV are
give rise to a stabilized carbonium ion, undergo selective acid-catalyzed rearrangements to 3-alkylated-1,2-benzoquinones 4. Aziridino-quinone 10c gives rise to the heterobicyclic 1,2-benzoquinone 11. When R1 does not contain groups capable of stabilizing a positive charge, efficient and selectiveN-dealkylations occur. The mechanisms of these reactions are discussed.