Adamantanethione and its reduction to 2-adamantanethiol

Abstract
Reaction of adamantanone with phosphorus pentasulfide affords the corresponding thioketone. This new, comparatively very stable alicyclic thione was also obtained by an indirect route from 2-ethoxy-2-adamantanethiol. Reduction of the thioketone with sodium borohydride yields 2-adamantanethiol.