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A generic diazirine

Diazirines are a class of organic molecules consisting of a carbon bound to two nitrogen atoms, which are double-bonded to each other, forming a cyclopropene-like ring. They are mainly used as carbene precursor and also in photoaffinity labelling studies of nucleic acids and proteins.[1]


Diazirines can be decomposed by using UV-light.

Diazirines are unstable in the presence of light, decaying upon photolysis to form the corresponding carbene and nitrogen gas. This reaction can also be performed thermally.


Diazirines can be synthesized by the Graham reaction, from the corresponding amidine or by oxidation of a diaziridine.


  1. ^ Photoactivatable Reagents Based on Aryl(trifluoromethyl)diazirines: Synthesis and Application for Studying Nucleic Acid–Protein Interactions; G. A. Korshunova, N. V. Sumbatyan, A. N. Topin, and M. T. Mtchedlidze, Molecular Biology, 2000, 34, 823-839. doi:10.1023/A:1026671624793
  • Chemistry of Diazirines, ed. Michael T.H. Liu, 1987. ISBN 978-0-8493-5047-4.
  • Valence Isomerization between Diazo Compounds and Diazirines, S.M. Korneev, Eur. J. Org. Chem., 2011, 31, 6153–6175, DOI: 10.1002/ejoc.201100224