Synthesis of New Sulfonic Acid Derivatives by the Reaction of S-(1S,2R,3S,5R)-2-Formyl-6,6-dimethylnorpinan-3-yl Thioacetate with Chlorine Dioxide
摘要
Abstract
New polyfunctional compounds of the pinane series, 2-carboxy-3-thioacetate, 2-carboxy-3-sulfonyl chloride, and 2-carboxy-3-sulfonic acid that are promising intermediate products in organic synthesis, were synthesized for the first time by the reaction of S-(1S,2R,3S,5R)-(6,6-dimethyl-2-formylnorpinan-3-yl) thioacetate with chlorine dioxide. The major reaction pathway in nonpolar solvents involves oxidation of the aldehyde group to carboxy, whereas oxidation of the sulfur atom, followed by deacetylation, occurs in highly polar solvents. The effect of VO(acac)2 as catalyst on the reaction chemoselectivity in weakly polar diethyl ether was revealed.