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NMR/NOE elucidation of the stereostructure of cycloadducts of acetonitrile oxide with norbornane/ene‐fused dihydro‐oxazines
Author(s) -
Sohár Pál,
Stájer Géza,
Szabó Angela E.,
Bernáth Gábor
Publication year - 1991
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260290713
Subject(s) - norbornane , chemistry , acetonitrile , cycloaddition , oxazines , adduct , nuclear magnetic resonance spectroscopy , norbornene , stereochemistry , 1,3 dipolar cycloaddition , medicinal chemistry , organic chemistry , polymer , monomer , catalysis
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 CC 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 CN 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.