The “nonsymmetry” of the 2-bornyl cation has been demonstrated in an ion pair for the first time. The local order in the ion pairs 1 and 2 was investigated using chiral, 18O-labeled p-toluenesulfinate. In 2, neither the oxygen atoms of the sulfinate nor C-1 and C-2 are equivalent. These results are of value in understanding the partial retention of configuration in the deamination reactions and HX additions of norbornenes.
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Kirmse et al. (1991) studied this question.
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