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40.1.3.1.4.1 Variation 1: Of Aziridines

DOI: 10.1055/sos-SD-040-00396

Feng, J. Q.; Li, C.-J.Science of Synthesis, (200940606.

The pyrolyses of 1-acetyl- and 1-benzoylaziridines yield allylic amides though stereospecific cis-eliminations analogous to the Chugaev reaction. For instance, when 1-acetyl-2,2-dimethylaziridine (83) is heated at reflux at atmospheric pressure, it is converted into N-(2-methylprop-2-enyl)acetamide (84) in 93% yield. This product may then be hydrolyzed to afford 2-methylprop-2-enamine (85) (Scheme 30).[‌110‌]

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