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Complete analysis of the 1H NMR spectra of acetylated glycals—a conformational study

✍ Scribed by M. Rico; J. Santoro

Publisher
John Wiley and Sons
Year
1976
Tongue
English
Weight
736 KB
Volume
8
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The complete analysis of the ^1^H NMR spectra of the six acetylated glycals as well as that of tetra‐O‐acetyl‐2‐hydroxy‐D‐glucal has been carried out. The conformation of these compounds, as determined from the proton couplings (±0.05Hz) obtained, has been interpreted in terms of a rapid interconversion equilibrium between the two possible dihydropyran half‐chair conformations. A computer treatment of all observed couplings has been carried out to obtain optimized values for the populations and couplings characteristic of the two alternative half‐chair conformations. The rotamer populations of the acetoxy–methyl group are discussed on the basis of the measured ^5^J~16~ and ^5^J~36~ couplings.

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