Studies on ring cleavage of aziridines with hydroxyl compounds

Ring cleavage of a variety of N-substituted aziridines has been studied with hydroxyl compounds (primary, secondary, allylic and tertiary). It was observed that the cleavage reaction was very facile in the presence of BF3·OEt2 and Sn(OTf)2. Whereas the aziridine opening reaction was facile with primary and secondary alcohols, hindered alcohols took longer (2 days). However, with the help of microwave radiation, the cleavage reaction with hindered alcohols could be achieved in a very short period (15 min). Phenols could only cleave aziridines under microwave irradiation.