Abstract
2-Arylthio- or 2-alkylthio-5-hydroxy-p-benzoquinones (XV-XXI) were easily synthesized by the oxidation of 4-arylthio- or 4-alkylthioresorcinols (VIII-XIV) with potassium nitrosodisulfonate. VIII-XIV were prepared from the sulfonium perchlorates (I-VII) synthesized by the reaction of resorcinol with sulfoxides. The structure of these hydroxybenzoquinones (XV-XXI) was elucidated. Further, the Thiele addition of acetic anhydride to 2-arylthio- or 2-alkylthio-p-benzoquinones was examined. Only in the case of the arylthio compounds, the Thiele reaction progressed smoothly to afford arylthiohydroxhydroquinone triacetates (XXX-XXXII). The position of the acetoxyl group in these compounds XXX-XXXII was determined.
