Stereostructure of cycloadducts of norbornane/ene‐fused dihydro‐1,3‐ and ‐3,1‐oxazines

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Abstract

The steric structures of the tetracyclic mono‐ and the pentacyclic bis‐adducts formed in the cycloadditions of norbornane‐ and norbornene‐fused 1,3‐ and 3,1‐dihydrooxazine dipolarophiles with diphenylnitrilimine or benzonitrile oxide were investigated. These reactions could yield 2–8 annellation and positional isomers. The structures of the products were proved by 1H and 13C NMR spectroseopy, and the various potentially stable conformations of the flexible hetero rings were evaluated. The assignments were confirmed by double resonance and DEPT measurements; the steric structures were supported by the results of DNOE experiments.

Original languageEnglish
Pages (from-to)635-641
Number of pages7
JournalMagnetic Resonance in Chemistry
Volume25
Issue number7
DOIs
Publication statusPublished - 1987

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Norbornanes
Cycloaddition
Isomers
Oxides
Conformations
Nuclear magnetic resonance
Experiments

Keywords

  • H, C NMR
  • 1,3‐ and 3,1‐oxazines
  • Configuration and Configuration
  • Cycloaddition
  • DNOE
  • isomerism
  • Mono‐ and bis‐adducts
  • Positional
  • Tetra‐ and penta‐cyclic norbornane/ene fused

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

Cite this

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title = "Stereostructure of cycloadducts of norbornane/ene‐fused dihydro‐1,3‐ and ‐3,1‐oxazines",
abstract = "The steric structures of the tetracyclic mono‐ and the pentacyclic bis‐adducts formed in the cycloadditions of norbornane‐ and norbornene‐fused 1,3‐ and 3,1‐dihydrooxazine dipolarophiles with diphenylnitrilimine or benzonitrile oxide were investigated. These reactions could yield 2–8 annellation and positional isomers. The structures of the products were proved by 1H and 13C NMR spectroseopy, and the various potentially stable conformations of the flexible hetero rings were evaluated. The assignments were confirmed by double resonance and DEPT measurements; the steric structures were supported by the results of DNOE experiments.",
keywords = "H, C NMR, 1,3‐ and 3,1‐oxazines, Configuration and Configuration, Cycloaddition, DNOE, isomerism, Mono‐ and bis‐adducts, Positional, Tetra‐ and penta‐cyclic norbornane/ene fused",
author = "P. Soh{\'a}r and G. St{\'a}jer and G. Bern{\'a}th",
year = "1987",
doi = "10.1002/mrc.1260250715",
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pages = "635--641",
journal = "Magnetic Resonance in Chemistry",
issn = "0749-1581",
publisher = "John Wiley and Sons Ltd",
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T1 - Stereostructure of cycloadducts of norbornane/ene‐fused dihydro‐1,3‐ and ‐3,1‐oxazines

AU - Sohár, P.

AU - Stájer, G.

AU - Bernáth, G.

PY - 1987

Y1 - 1987

N2 - The steric structures of the tetracyclic mono‐ and the pentacyclic bis‐adducts formed in the cycloadditions of norbornane‐ and norbornene‐fused 1,3‐ and 3,1‐dihydrooxazine dipolarophiles with diphenylnitrilimine or benzonitrile oxide were investigated. These reactions could yield 2–8 annellation and positional isomers. The structures of the products were proved by 1H and 13C NMR spectroseopy, and the various potentially stable conformations of the flexible hetero rings were evaluated. The assignments were confirmed by double resonance and DEPT measurements; the steric structures were supported by the results of DNOE experiments.

AB - The steric structures of the tetracyclic mono‐ and the pentacyclic bis‐adducts formed in the cycloadditions of norbornane‐ and norbornene‐fused 1,3‐ and 3,1‐dihydrooxazine dipolarophiles with diphenylnitrilimine or benzonitrile oxide were investigated. These reactions could yield 2–8 annellation and positional isomers. The structures of the products were proved by 1H and 13C NMR spectroseopy, and the various potentially stable conformations of the flexible hetero rings were evaluated. The assignments were confirmed by double resonance and DEPT measurements; the steric structures were supported by the results of DNOE experiments.

KW - H, C NMR

KW - 1,3‐ and 3,1‐oxazines

KW - Configuration and Configuration

KW - Cycloaddition

KW - DNOE

KW - isomerism

KW - Mono‐ and bis‐adducts

KW - Positional

KW - Tetra‐ and penta‐cyclic norbornane/ene fused

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