The Synthesis of N-Benzoyl Aziridines from β-Benzamidoalkyl Phenyl Selenides

Abstract

β-Benzamidoalkyl phenyl selenides can be oxidised, using mCPBA, to the corresponding selenones which can be cyclised to oxazolines or aziridines depending on the reaction conditions. In neutral or weakly basic conditions the oxazoline is the major product but if the oxidation is conducted at − 60°C then the corresponding aziridine is formed in high yields using strongly hasic conditions. The synthesis of a range of bicyclic N-benzoyl aziridines is described.

Key Words:

• selenides
• selenones
• oxazolines
• aziridines