Stereoselective oxidation of phenoxathiin-based thiacalix[4]arenes - stereomutation of sulfoxide groups

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F23%3A43927606" target="_blank" >RIV/60461373:22310/23:43927606 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22810/23:43927606

Result on the web

<a href="https://pubs.rsc.org/en/content/articlelanding/2023/OB/D3OB00530E" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2023/OB/D3OB00530E</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d3ob00530e" target="_blank" >10.1039/d3ob00530e</a>

Result language

angličtina

Original language name

Stereoselective oxidation of phenoxathiin-based thiacalix[4]arenes - stereomutation of sulfoxide groups

Original language description

A phenoxathiin-based macrocycle represents an inherently chiral building block, well accessible in two steps from the starting thiacalix[4]arene. The oxidized derivatives bearing one sulfoxide group and three sulfonyl groups were found to exhibit unexpected stereochemical preferences of the sulfoxide group during transformations. The sulfoxide moiety is always pointing out of the cavity (S = O out), while the opposite (S O in) configuration was never obtained by direct oxidation. In order to achieve full oxidation to sulfone, the configuration of the sulfoxide group must first be changed by a photochemical inversion before the final oxidation occurs. The phenomenon of stereomutation of the sulfoxide group in the thiacalixarene series was studied using a combination of experimental (NMR and single crystal X-ray analysis) and theoretical (DFT) approaches. © 2023 The Royal Society of Chemistry.

Czech name

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Czech description

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Type

J_SC - Article in a specialist periodical, which is included in the SCOPUS database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA20-08667S" target="_blank" >GA20-08667S: Chemistry of phenoxathiin-based thicalixarenes and related compounds</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2023

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

ORGANIC &amp; BIOMOLECULAR CHEMISTRY

ISSN

1477-0520

e-ISSN

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Volume of the periodical

21

Issue of the periodical within the volume

22

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

4620-4630

UT code for WoS article

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EID of the result in the Scopus database

2-s2.0-85160427481