Blum-Ittah Aziridine Synthesis

• General Characteristics

Epoxides can be converted into aziridines by nucleophilic attack of azide ion, the Staudinger reaction, and aziridine ring formation with elimination of triphenylphosphine oxide.

• General References

• Ittah, Y.; Shahak, I.; Blum, J. J. Org. Chem. 1978, 43, 397. DOI: 10.1021/jo00397a004
  
• Ittah, Y.; Sasson, Y.; Shahak, I.; Tsaroom, S.; Blum. J. J. Org. Chem. 1978, 43, 4271. DOI: 10.1021/jo00416a003

• Reaction Mechanism

The Staudinger azide reduction and elimination of PPh₃=O leads to the formation of aziridines. Note that both C-N bond forming steps are stereospecific S_N2 displacement.

• Examples

• Experimental Procedure

• Experimental Tips

• References

• Related Reactions

• Related Books

• External Links

Aziridines in Synthesis (PDF, Baran’s group)

synthesis of aziridines from epoxides