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

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 -(1 S ,2 R ,3 S ,5 R )-(6,6-dimethyl-2-form...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2024-04, Vol.60 (4), p.611-619
Main Authors: Subbotina, S. N., Grebyonkina, O. N., Gribkov, P. V., Gerasimova, D. P., Lodochnikova, O. A., Gilfanov, I. R., Nikitina, L. E., Lezina, O. M., Rubtsova, S. A.
Format: Article
Language:English
Subjects:
Aldehydes
Chemistry
Chemistry and Materials Science
Chlorine dioxide
Diethyl ether
Organic Chemistry
Oxidation
Solvents
Sulfonic acid
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Summary: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 -(1 S ,2 R ,3 S ,5 R )-(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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428024040079