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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60461373:22810/23:43927606

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_SC - Článek v periodiku v databázi SCOPUS

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA20-08667S" target="_blank" >GA20-08667S: Chemie thiacalixarenů na bázi phenoxathiinu a příbuzných látek</a><br>

Návaznosti

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

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

ORGANIC &amp; BIOMOLECULAR CHEMISTRY

ISSN

1477-0520

e-ISSN

—

Svazek periodika

21

Číslo periodika v rámci svazku

22

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

4620-4630

Kód UT WoS článku

—

EID výsledku v databázi Scopus

2-s2.0-85160427481