6588-78-9Relevant articles and documents
Synthesis and Oxidation of Myrtanethiol and Its Functional Derivatives with Chlorine Dioxide
Grebyonkina,Lezina,Izmest’ev,Frolova,Rubtsova,Kutchin
, p. 1469 - 1475 (2019/12/28)
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.
The use of sulfides derived from carane, p -menthane, pinane, and bornane in the synthesis of optically active epoxides
Banach, Anna,Scianowski, Jacek,Ozimek, Piotr
, p. 274 - 284 (2014/01/06)
Convenient routes for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane, p-menthane, pinane, and bornane were developed. Methyl and dimonoterpenyl sulfides have been obtained by the reaction of the corresponding monoterpene thiolates with methyl iodide or monoterpene tosylates. The reactions of monoterpene tosylates with sodium benzenethiolate gave the corresponding phenyl monoterpenyl sulfides. These sulfides were used for the sulfur ylide-mediated reaction to yield epoxides. Good diastereoselectivities up to 99:1 and low to moderate enantioselectivities were observed for the enantioselective synthesis of chiral epoxides.
