Stable but chimeric antiaromatic 1H-azirines? A threefold reinvestigation

Three different reports on the syntheses of isolable 1H-azirines 6, 15, and 21 were reinvestigated. Instead of the claimed heterocyclic product 6, the isomeric thiazole derivative 7 has been isolated now with nearly identical yield. In the case of the asserted bicyclic 1H-azirine 15, the corrected structure includes the isomeric 3-aminomaleimide moiety of 18. A mechanism to explain the formation of this substance is suggested. The isolation of the antiaromatic compound 21 has also to be rejected. Thus, 1H-azirines keep their classification as very elusive high-energy intermediates.

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