3-Benzoyloxaziranes; a new rearrangement to substituted N,N-diacylamines

✍ Scribed by Albert Padwa

• Publisher: Elsevier Science
• Year: 1964
• Tongue: French
• Weight: 191 KB
• Volume: 5
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75131-8

✦ Synopsis

Although oxaziranes have received considerable attention, there exists no authenticated preparation of a 3 -acyloxazirane lgZs3 (II). such compounds are threemembered carbon-nitrogen-oxygen ring analogs of a, Gepoxyketones. In view of the many polar rearrangements exhibited by the latter class of compounds, it became of interest to determine whether 3-acyloxaziranes would undergo related transformations. Treatment of the mono-anil of benzil (Ia) with metachloroperhenzoic acid or anhydrous peracetic acid in methylene chloride afforded in excellent yield a product 1 W. D. Emmons. J. Am. Chem. Sot., 2. 6208 (1956); 79& 5739 (1957).