Science of Synthesis

Sweeney, J. B., Science of Synthesis, (2009) 40, 683.

Other than simple (usually symmetrical) aziridines, azirines are most often precursors to polycyclic aziridines in which the nitrogen atom is located at a ring junction; the azirine acts as a heterodienophile in cycloaddition reactions, though the C=N bond is sometimes rather unreactive in these processes. 2-Aryl-2H-azirine-3-carboxylates (e.g., ‌127‌) react with 2,3-dimethylbuta-1,3-diene to give bicyclo[4.1.0]heptenecarboxylates (e.g., ‌152‌, ‌Scheme 86‌), but the diene must be present in large excess.[‌231‌] In the case of chiral enantiomerically pure (2-aryl-2H-azirin-3-yl)phosphonates (e.g., ‌153‌), Diels–Alder reactions are slow when simple dienes are used; as might be expected given the intimate juxtaposition with preexisting chirality, the reactions are diastereoselective.[‌232‌] (2-Oxooxazolidinyl)dienes, such as ‌154‌, undergo cycloaddition with 2H-azirines, without the need for a large excess of the diene. Chiral oxazolidinone substituents do not induce diastereoselective reaction.[‌233‌]

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References

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• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.