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.

Autor:	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.
Předmět:	SULFONIC acid derivatives CHLORINE dioxide SULFONIC acids POLAR solvents AMMONIUM acetate ETHER (Anesthetic) ORGANIC synthesis
Zdroj:	Russian Journal of Organic Chemistry; Apr2024, Vol. 60 Issue 4, p611-619, 9p
Abstrakt:	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) thio-acetate 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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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