ChemInform Abstract: Reactivity of 1,3-Di-tert-butylaziridinones with Phenyl Substituents. A New Fragmentation of α-Lactams.

✍ Scribed by M. SHIMAZU; Y. ENDO; K. SHUDO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199741132

✦ Synopsis

Reactivity of 1,3-Di-tert-butylaziridinones with Phenyl Substituents. A New Fragmentation of α-Lactams.

-Dehydrohalogenation of N-alkyl-α-haloamides (I) with KOH/18-crown-6 provides the aziridinones (II) with bulky substituents. Their decomposition in refluxing methanol gives the expected amides. However, the aziridinones (IIa) and (IIb) with a phenyl group on the C3-moiety show a new fragmentation to 2-methyl-1-phenylpropene (V) and isocyanates which are isolated as the amides (VI). Reaction of (II) with methoxide or benzylamine yields the expected products. -(SHIMAZU, M.;