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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)

✍ Scribed by Katri Laihia; Erkki Kolehmainen; Petteri Malkavaara; Jorma Korvola; Pia Mänttäri; Reijo Kauppinen

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
483 KB
Volume
30
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

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 ^1^H, ^13^C and ^17^O NMR spectra were measured, analysed and assigned. The ^1^H NMR spectral parameters were obtained by computer‐aided analyses of the very complex multi‐spin, second‐order spectra. Some of the ^13^C NMR chemical shift assignments of these compounds reported in the literature should be changed, based on these accurate ^1^H NMR spectral analyses and carbon‐proton chemical shift correlated spectra (COSY). The new assignments are supported by the ^1^J(C, H) values, which show a strong dependence on the bond angle and the steric strain of the ring system concerned.

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