Abstract 2,7-Dicarboxytriptycene retaining C2-axis of symmetry was synthesized from 1,5-dichloroanthraquinone. Optical resolution of the triptycene afforded (+)- and (−)-enantiomers. The absolute configuration of (+)-2,7-dicarboxytriptycene was determined as 1R,6R by chemical correlation with (+)-2-methoxy-7-methoxycarbonyltriptycene which has 1R,6S configuration as confirmed by chemical transformation and X-ray structure analysis using the Bijvoet method. Starting from (+)-2,7-dicarboxytriptycene, a series of 2,7-disubstituted triptycenes having 1R,6R configuration has been prepared.
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Kuritani et al. (1973) studied this question.
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