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Carbon-13 n.m.r. studies: 68—diastereomeric nonequivalence and the characterization of some bisnorbornylpinacols

✍ Scribed by J. B. Stothers; K. C. Teo

Publisher
John Wiley and Sons
Year
1977
Tongue
English
Weight
403 KB
Volume
9
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The sodium‐ammonia reduction of racemic norcamphor, exo‐3‐methylnorcamphor and 3,3‐dimethyl‐norcamphor (camphenilone) leads to substantial yields (60–90%) of the corresponding 2,2′‐bisnorbornyl‐2,2′‐diols as diastereomeric mixtures. A combination of their ^1^H, ^13^C and infrared spectra together with the results of periodic acid and lead tetraacetate oxidations permits stereochemical assignments for these six pinacols.

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