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Steric inhibition of the rotation of the phenyl groups in 2,6-dimethyl-1-phenylcyclohexanol and dendrocrepine detected by means of carbon-13 nuclear magnetic resonance

✍ Scribed by Edward Leete; Robert M. Riddle

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
203 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the course of an investigation on the biosynthesis of the alkaloids of the orchid

Dendmbiwn orepidatwn

Lindl. we examined the 13C NMR spectrum of dendrocrepine (A).2'3 The chemical shifts (ppm from Me4Si in CDC13) indicated on formula 1, were assigned by offresonance decoupling, and by comparison with the spectra of indolizidine and methylpiperidines. To our surprise, the phenyl groups gave rise to six resonances. An examination of space-filling models indicated that the non-equivalence of the two ortho and two meta positions could be due to lack of rotation of the phenyl groups. We have thus examined the 206.7 i==()

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✍ C. Rabiller; G. J. Martin; J. P. Pradere; J. C. Meslin; H. Quiniou 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 English ⚖ 471 KB

## Abstract The influence of substituents in a new series of 2__H__‐thiopyrans, 2__H__‐thiopyran‐2‐ones (thiones) and their thiazine analogues is examined by means of carbon (^13^C) and nitrogen (^15^N) NMR. A linear relationship is shown to exist between the chemical shifts (δ~13C~ or δ~15N~) of t