Oxa-6-thia-adamantanes Pathway

By transannular addition of sulfur dichloride to 9-oxabicyclo[3.3.1]nonan-2,6-diene 

6-thia-adamantane (25) . On the other hand, the dichloride 24 could be transformed almost quantitatively into the 8°0).diol 25 which consequently was acetylated to the diacetate 2d and methylated to the dimethoxy compound 27 K Oxidation of diol 25 with hydrogen peroxide in acetic acid led depending on the reaction conditions either to sulfoxide 29 or directly to the corresponding sulfone from which also the diacetate S2 was prepared. The sulfones 30 (R = Cl) and 33 (R = H) were obtained by analogous oxidation of the corresponding sulfides 24 and 28  

---