NMR/NOE Elucidation of the Stereostructure of Cycloadducts of Acetonitrile Oxide with Norbornane/ene-Fused Dihydro-oxazines

Article abstract of DOI:10.1002/mrc.1260290713

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 1H and 13C NMR spectroscopy, making use of DNOE experiments.