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9.5 Product Class 5: 1H-Azirines

DOI: 10.1055/sos-SD-009-00047

Zeller, K.-P.Science of Synthesis, (2001967.

Depending on the position of the ring double bond, two isomeric azirine sructures are possible. To distinguish the two azirine isomers 1 and 2 (Scheme 1), The Ring Index[‌1‌] and CAS apply the "indicated hydrogen" nomenclature and designate 1 and 2 as 1H-azirine and 2H-azirine, respectively. This system is also adopted here. Parallel to this naming practice, a designation to indicate the position of the double bond is widely used. With this system the names of 1 and 2 are 2-azirine and 1-azirine, respectively. It is obvious that the two competing nomenclatures may produce confusion. A cautionary note should be added to the CAS practice of naming arene imines. Such molecules, which are fused aziridines, are named as azirine derivatives, e.g. compound 3[‌2‌] is named 5,5a-dihydro-4bH-dibenz[3,4:5,6]anthra[1,2-b]azirine.

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