Abstract
The course of the reactions that occur when stereochemically rigid trans-perhydronaphthalene1,4-diol monosulfonate esters (1-0) are treated with alkali metal tert-amylate in refluxing benzene depends on the relative orientation of the leaving group and the tertiary hydroxyl group. An equatorial sulfonate ester group favors homofragmentation leading to the cyclopropane derivative 15. In case of an axial sulfonate ester group β-elimination, which strongly depends on the stereochemistry of the tertiary deprotonated hydroxyl group, is the main reaction path
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