Vinylaziridine 2 undergoes reaction with electrophilic acetylenes and olefins to produce 7-membered azepine derivatTves. With B-nitro-styrene however, a novel rearrangement occurs, presumably via an ene reaction to form lD\_, the structure of which is definitively shown by x-ray diffraction. Cis-1,2
A novel rearrangement of an aminoőxy compound
✍ Scribed by Leo A. Paquette
- Publisher
- Elsevier Science
- Year
- 1962
- Tongue
- French
- Weight
- 178 KB
- Volume
- 3
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A SIZEABLE body of evidence has now accumulated suggesting that a number Of rearrangement reactions proceed via three-membered nitrogen-containing rings.
For example, the Neber rearrangement of ketoxime tosylates, 1 the rearrangement of N,N-dichloro-set-alkylamines, 2-4 and the synthesis of a-amino ketones and acids from N-chloroketimines' have in common the azirine intermediate A (or some closely related aziridine derivative).
📜 SIMILAR VOLUMES
Oxidative rearrangement of dihydronaphthofuran 5 with aqueous ceric ammonium nitrate afforded the cage compound 7 which decomposed to diol 8 upon standing at room temperature. An X-ray structure obtained for diol 8 confirmed the formation of this novel cage structure.