Synthesis and Reactions of New Tellurium-substituted Terpenyl Compounds

In recent years, chalcogenides were widely used as efficient reagents and catalysts to create new carbon-oxygen, carbon-nitrogen and carbon-carbon bonds. Our previous research was focused on developing effective methods for the synthesis of new optically active organosulfur and organoselenium compounds derived from monoterpenes. Satisfying results prompted us to synthesize tellurium analogues. We have developed new methodologies for the synthesis of terpene ditellurides, tellurides, methyl terpenyl tellurides, and phenyl terpenyl tellurides from p-menthane, carane and pinane systems. The synthesis was based on the reaction of sodium telluride, sodium ditelluride, sodium benzenetellurolate, and sodium methanetellurolate with terpene tosylates, chlorides and epoxides. Additionally, terpene tellurides were converted in situ to telluronium ylides, and were used as reagents in asymmetric epoxydation. The best selectivity of epoxidation reaction was achieved for dicaranyl telluride.