1H, 13C and 17O NMR spectroscopic study of four bicyclo [3.1.1]heptenes (derivatives of α‐pinene) and four bicyclo[3.1.1]heptanes (derivatives of β‐pinene)

@article{Laihia19921H1A,
  title={1H, 13C and 17O NMR spectroscopic study of four bicyclo [3.1.1]heptenes (derivatives of α‐pinene) and four bicyclo[3.1.1]heptanes (derivatives of β‐pinene)},
  author={K. Laihia and E. Kolehmainen and P. Malkavaara and J. Korvola and P. M{\"a}ntt{\"a}ri and R. Kauppinen},
  journal={Magnetic Resonance in Chemistry},
  year={1992},
  volume={30}
}
Four derivatives of 2, 6, 6‐trimethylbicyclo[3.1.1]hept‐2‐ene (α‐pinene) and four derivatives of 2‐methylene‐6, 6‐dimethylbicyclo[3.1.1]heptane (β‐pinene) were synthesized and their 1H, 13C and 17O NMR spectra were measured, analysed and assigned. The 1H NMR spectral parameters were obtained by computer‐aided analyses of the very complex multi‐spin, second‐order spectra. Some of the 13C NMR chemical shift assignments of these compounds reported in the literature should be changed, based on… Expand
View on Wiley
11 Citations
Highly Influential Citations
1

11 Citations

Citation Type

Citation Type

13C NMR chemical shift assignment based on 13C INADEQUATE and heteronuclear 13C, 1H-COSY experiments and absolute configuration of a new chiral pentacyclic pinocarvone dimer
  • 7
Oxygen-containing bicyclic monoterpenes. 1H, 13C and 17O NMR Spectroscopic and X-ray diffraction studies of seven oxidation products of (+)-3-carene
  • 9
(+)- and (-)-α-Pinene as chiral recognition probes withnatural cyclodextrins and their permethylated derivatives. An aqueousNMR study
  • 13
NMR manifestations and molecular dynamics modeling of chiral recognition of α-pinenes by α-cyclodextrin
  • 20
DFT studies of the conformational/structural dependencies of geminal 1H,1H scalar coupling 2J(H,H′) in substituted methanes
  • M. Barfield
  • Chemistry, Medicine
  • Magnetic resonance in chemistry : MRC
  • 2007
  • 6
Will the real β‐pinene please stand up
  • 4
Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal.
  • 1
Lactones, 2. Synthesis of Enantiomeric Pairs of Lactones with the Pinane or the Fenchane system
  • 9
Dolabella‐3,7,18‐triene, the main constituent of the essential oil of the white lotus flower (Nymphaea lotus, Nymphaeaceae)
  • 2
Profiling Of Terpene Metabolism in 13CO2-Labelled Thymus Transcaucasicus
  • 6
  • Highly Influenced
  • PDF
...
1
2
...

References

SHOWING 1-10 OF 25 REFERENCES
The octant rule. XIV. synthesis and circular dichroism of α- and -deuteriobicyclo[3.2.1]octan-3-one and 6,6-dimethybicyclo[3.1.1]heptan-3-one
  • 10
Conformational studies of monoterpenes. II–conformational studies of bicyclo[3.1.1]heptane derivatives by 13C NMR
  • 16
The use of shift reagents and 13C nuclear magnetic resonance for assignment of stereochemistry to oximes
  • 14
The NMR spectra and conformations of cyclic compoundsV: Proton couplings and chemical shifts in bridged cyclobutanes
  • 31
The NMR spectra and conformations of cyclic compounds—VII: The conformations of β-pinene, pinocarvone and the cis- and trans-pinocarveols†
  • 15
A revised assignment of the13C NMR spectra of a- and -pinenes
  • 7
Vicinal C,H spin coupling in substituted alkenes. Stereochemical significance and structural effects†‡
  • 190
Photochemistry of nitroso derivatives in solution—XXX: Temperature effects on radical additions to terpenes and reactions of 2-ammonium nitrosoalkanes
  • 7
13C NMR of camphene and α‐pinene: Revised assignments
  • 15
Carbon-13 nuclear magnetic resonance spectra of pinane monoterpenoids
  • 20
...
1
2
3
...