Three diastereomeric hydrocarbons 7 were formed on reaction of 1‐adamantyl‐1,1‐dibromo‐2,2‐dimethylpropane with magnesium. They were separated by fractional crystallization and identified by 1H NMR spectroscopy and X‐ray crystallography as meso‐7 and the two rotamers of D,L‐7 mentioned in the title. They are the first examples of simple aliphatic hydrocarbon rotamers, which do not interconvert at room temperature and above. Analogous 1‐norbornyl derivatives were also obtained but could not be separated. The kinetics and the products of thermolysis of these hydrocarbons were investigated.
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Meer et al. (1986) studied this question.
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