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

Research output: Contribution to journalArticle

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

Fingerprint

Norbornanes
Cycloaddition
Acetonitrile
Nuclear magnetic resonance spectroscopy
Nuclear magnetic resonance
Molecules
Oxides
Experiments
acetonitrile oxide
2-norbornene

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)

Cite this

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title = "NMR/NOE elucidation of the stereostructure of cycloadducts of acetonitrile oxide with norbornane/ene‐fused dihydro‐oxazines",
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.",
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author = "P. Soh{\'a}r and G. St{\'a}jer and Szab{\'o}, {Angela E.} and G. Bern{\'a}th",
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T1 - NMR/NOE elucidation of the stereostructure of cycloadducts of acetonitrile oxide with norbornane/ene‐fused dihydro‐oxazines

AU - Sohár, P.

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Bernáth, G.

PY - 1991

Y1 - 1991

N2 - 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.

AB - 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.

KW - H and C NMR

KW - Cycloaddition of acetonitrile oxide to norbornane/ene‐fused dihydro‐1,3‐oxazines

KW - DNOE

KW - Regioselectivity

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