Tetrahedron Letters

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

K Banert, S Bochmann, M Hagedorn, F Richter

Index: Banert, Klaus; Bochmann, Sandra; Hagedorn, Manfred; Richter, Frank Tetrahedron Letters, 2013 , vol. 54, # 46 p. 6185 - 6188

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Citation Number: 6

Abstract

Abstract 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 ...