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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 1H, 13C 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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Stothers et al. (1977) studied this question.
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