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

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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.

About the authors

S. N. Subbotina

Institute of Chemistry, Federal Research Center, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: lezina-om@yandex.ru
ORCID iD: 0009-0001-0512-3478
Russian Federation, ul. Pervomayskaya, 48, Syktyvkar, 167000

O. N. Grebyonkina

Institute of Chemistry, Federal Research Center, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: lezina-om@yandex.ru
ORCID iD: 0000-0002-1982-104X
Russian Federation, ul. Pervomayskaya, 48, Syktyvkar, 167000

P. V. Gribkov

Institute of Chemistry, Federal Research Center, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: lezina-om@yandex.ru
ORCID iD: 0000-0003-2923-4620
Russian Federation, ul. Pervomayskaya, 48, Syktyvkar, 167000

D. P. Gerasimova

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences

Email: lezina-om@yandex.ru
ORCID iD: 0000-0001-9770-196X
Russian Federation, ul. Arbuzova, 8, Kazan, 420088

O. A. Lodochnikova

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences

Email: lezina-om@yandex.ru
ORCID iD: 0000-0001-9614-5092
Russian Federation, ul. Arbuzova, 8, Kazan, 420088

I. R. Gilfanov

Kazan National Research Technological University

Email: lezina-om@yandex.ru
ORCID iD: 0000-0003-4351-3378
Russian Federation, ul. K. Marksa, 68, Kazan, 420015

L. E. Nikitina

Kazan State Medical University

Email: lezina-om@yandex.ru
ORCID iD: 0000-0003-2113-5732
Russian Federation, ul. Butlerova, 49, Kazan, 420012

O. M. Lezina

Institute of Chemistry, Federal Research Center, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: lezina-om@yandex.ru
ORCID iD: 0000-0002-6105-5641
Russian Federation, ul. Pervomayskaya, 48, Syktyvkar, 167000

S. A. Rubtsova

Institute of Chemistry, Federal Research Center, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: lezina-om@yandex.ru
ORCID iD: 0000-0003-1224-8751
Russian Federation, ul. Pervomayskaya, 48, Syktyvkar, 167000

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