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

P. Sohár, G. Stájer, Angela E. Szabó, G. Bernáth

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7 Citations (Scopus)

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

Original languageEnglish
Pages (from-to)706-710
Number of pages5
JournalMagnetic Resonance in Chemistry
Volume29
Issue number7
DOIs
Publication statusPublished - 1991

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Keywords

  • H and C NMR
  • Cycloaddition of acetonitrile oxide to norbornane/ene‐fused dihydro‐1,3‐oxazines
  • DNOE
  • Regioselectivity

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

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