NMR/NOE elucidation of the stereostructure of cycloadducts of acetonitrile oxide with norbornane/ene-fused dihydro-oxazines

✍ Scribed by Pál Sohár; Géza Stájer; Angela E. Szabó; Gábor Bernáth

• Book ID: 102529543
• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 487 KB
• Volume: 29
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260290713

✦ Synopsis

Abstract

Norbornane‐di‐endo‐ and ‐di‐exo‐fused dihydro‐1,3‐oxazines underwent cycloaddition with in situ prepared acetonitrile oxide to yield tetracyclic 1,2,4‐oxadiazolines. Either the CC bond of the double dipolarophiles with the norbornene skeleton was saturated to give isoxazoline regioisomers, or a second molecule of the dipole added to the CN bond, resulting in the formation of a bis‐adduct. The structures of the products were confirmed by ^1^H and ^13^C NMR spectroscopy, making use of DNOE experiments.