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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Resumo

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.

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Sobre autores

S. 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
Rússia, ul. Pervomayskaya, 48, Syktyvkar, 167000

O. 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
Rússia, ul. Pervomayskaya, 48, Syktyvkar, 167000

P. 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
Rússia, ul. Pervomayskaya, 48, Syktyvkar, 167000

D. 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
Rússia, ul. Arbuzova, 8, Kazan, 420088

O. 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
Rússia, ul. Arbuzova, 8, Kazan, 420088

I. Gilfanov

Kazan National Research Technological University

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

L. Nikitina

Kazan State Medical University

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

O. Lezina

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

Autor responsável pela correspondência
Email: lezina-om@yandex.ru
ORCID ID: 0000-0002-6105-5641
Rússia, ul. Pervomayskaya, 48, Syktyvkar, 167000

S. 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
Rússia, ul. Pervomayskaya, 48, Syktyvkar, 167000

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2. Scheme

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3. Fig. 1. Geometry of two independent molecules in the crystal of sulfochloride 3b according to X-ray diffraction data

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4. Fig. 2. Asymmetric part of the cell of the complex (Na+4b–)·2H2O according to X-ray diffraction data

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5. Fig. 3. Fragment of the crystal packing of the complex (Na+4b–)⋅2H2O

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6. Figure from Contents

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