Optimizing Aziridination of Alkenes to Develop an Instruction-Friendly Experiment

The aziridine ring is a versatile building block for organic synthesis. Many biologically active compounds such as amino acids, beta-lactam antibiotics, and alkaloids have been derived from aziridines. Incorporating aziridine synthesis into an undergraduate organic chemistry lab course would provide students valuable experience and insight into a current synthesis methodology with many contemporary applications. A survey of reported aziridine ring syntheses was conducted to identify a procedure that accommodated instruction-related limitations that include cost, safety, time, and sophistication. This work focused on a methodology using pyridinium hydrobromide perbromide as a catalyst for aziridination of alkenes using chloramineT.