Diazirine

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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]

Reactions[edit]

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.

Synthesis[edit]

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

References[edit]

  • 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
  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