The oxidation of monoterpene thiols with chlorine dioxide afforded new water-soluble sulfonic acids and their derivatives (sulfonothioates and sulfonyl chlorides). The reaction of terpene thiols with ClO₂ gave the corresponding trisulfides. Sulfonothioates with a pinane skeleton showed antibacterial and antifungal activity.

Reactions of isobornane and pinane hydroxy thiols with chlorine dioxide have been studied. Unlike pinane derivatives, hydroxy thiols of the isobornane series reacted with chlorine dioxide to give the corresponding sulfinyl derivatives with high stereoselectivity. New terpenoids containing sulfur, oxygen, and chlorine atoms have been synthesized by oxidation of hydroxy thiols with chlorine dioxide.

Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)₂ catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed.

Reactions of pinane-10-sulfonyl chlorides with alkyl-, aryl-, and hetarylamines afforded up to 92% of new chiral sulfonamides that are potentially biologically active compounds.