Synthesis and Oxidation of Myrtanethiol and Its Functional Derivatives with Chlorine Dioxide

Abstract

cis-Myrtanethiol and a mixture of diastereoisomeric myrtanethiols were synthesized starting from (-)-β-pinene. Their oxidation with chlorine dioxide afforded a number of derivatives such as disulfides, S-thiol-sulfonates, sulfonyl chlorides, and sulfonic acids. The effects of reaction conditions (solvent nature, reactant molar ratio, reaction time, catalyst) on the yield and ratio of the products were studied. The corresponding sulfonyl chloride was obtained in quantitative yield by oxidation of thiol in the presence of vanadyl acetyl-acetonate, and optimal conditions were found for quantitative formation of myrtanesulfonic acid.