The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F23%3A43927774" target="_blank" >RIV/60461373:22310/23:43927774 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22810/23:43927774

Výsledek na webu

<a href="https://www.mdpi.com/1420-3049/28/9/3914" target="_blank" >https://www.mdpi.com/1420-3049/28/9/3914</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules28093914" target="_blank" >10.3390/molecules28093914</a>

Jazyk výsledku

angličtina

Název v původním jazyce

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

Popis výsledku v původním jazyce

Thiacalix[4]arene monosulfoxide 4 possesses a very unusual chemistry, as demonstrated by several unprecedented derivatives in calixarene chemistry. Interestingly, compound 4 cannot be prepared by the dealkylation of its corresponding tetramethoxy derivative using BBr3. Instead, the borate complex is formed with a boron bound by the two neighboring phenolic oxygens and a sulfoxide group. A similar type of borate complex with a spirodienone fragment was then isolated as a by-product. The oxidation of monosulfoxide with Chloramine-T did not provide the expected spirodienone moiety, but rather a complex oxathiane-based spiroheterocyclic part containing a chlorine atom. X-ray analyses confirmed the structures of the unusual products and feasible formation mechanisms were proposed. These results provide further evidence of the distinction between thiacalixarene chemistry and the chemistry of classical CH2 analogues. © 2023 by the authors.

Název v anglickém jazyce

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

Popis výsledku anglicky

Thiacalix[4]arene monosulfoxide 4 possesses a very unusual chemistry, as demonstrated by several unprecedented derivatives in calixarene chemistry. Interestingly, compound 4 cannot be prepared by the dealkylation of its corresponding tetramethoxy derivative using BBr3. Instead, the borate complex is formed with a boron bound by the two neighboring phenolic oxygens and a sulfoxide group. A similar type of borate complex with a spirodienone fragment was then isolated as a by-product. The oxidation of monosulfoxide with Chloramine-T did not provide the expected spirodienone moiety, but rather a complex oxathiane-based spiroheterocyclic part containing a chlorine atom. X-ray analyses confirmed the structures of the unusual products and feasible formation mechanisms were proposed. These results provide further evidence of the distinction between thiacalixarene chemistry and the chemistry of classical CH2 analogues. © 2023 by the authors.

Druh

J_imp - Článek v periodiku v databázi Web of Science

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

MOLECULES

ISSN

1420-3049

e-ISSN

1420-3049

Svazek periodika

28

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

LT - Litevská republika

Počet stran výsledku

17

Strana od-do

—

Kód UT WoS článku

000986784000001

EID výsledku v databázi Scopus

2-s2.0-85159329816