Regio- and stereoselectivity of spirodienone formation in 2,14-dithiacalix[4]arene

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43923404" target="_blank" >RIV/60461373:22310/21:43923404 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlepdf/2021/nj/d1nj01257f" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2021/nj/d1nj01257f</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d1nj01257f" target="_blank" >10.1039/d1nj01257f</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Regio- and stereoselectivity of spirodienone formation in 2,14-dithiacalix[4]arene

Popis výsledku v původním jazyce

The oxidation of 2,14-dithiacalix[4]arene with formation of the corresponding mono- and di-spirodienone derivatives was studied to find out which part of the molecule determines the chemical behaviour of this mixed-bridge macrocycle. Interestingly, applying procedures well established in thia- and/or classical calixarene chemistry, for the macrocycle with alternating thiacalixarene and calixarene structural fragments, resulted in the selective formation of the S-spiro derivative. Similar selectivity was also observed for dispiro compounds, indicating that the thiacalixarene fragment (Ar–S–Ar) is much more prone to spirocyclization than the calixarene one (Ar–CH2–Ar). The acid-induced rearrangement of the S-spiro compound led to the corresponding phenoxathiin-based calixarene, representing a novel macrocyclic system. The conformational preferences of the new inherently chiral macrocycles were studied with NMR spectroscopy and singlecrystal X-ray analysis complemented by DFT calculations.

Název v anglickém jazyce

Regio- and stereoselectivity of spirodienone formation in 2,14-dithiacalix[4]arene

Popis výsledku anglicky

The oxidation of 2,14-dithiacalix[4]arene with formation of the corresponding mono- and di-spirodienone derivatives was studied to find out which part of the molecule determines the chemical behaviour of this mixed-bridge macrocycle. Interestingly, applying procedures well established in thia- and/or classical calixarene chemistry, for the macrocycle with alternating thiacalixarene and calixarene structural fragments, resulted in the selective formation of the S-spiro derivative. Similar selectivity was also observed for dispiro compounds, indicating that the thiacalixarene fragment (Ar–S–Ar) is much more prone to spirocyclization than the calixarene one (Ar–CH2–Ar). The acid-induced rearrangement of the S-spiro compound led to the corresponding phenoxathiin-based calixarene, representing a novel macrocyclic system. The conformational preferences of the new inherently chiral macrocycles were studied with NMR spectroscopy and singlecrystal X-ray analysis complemented by DFT calculations.

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

2021

Kód důvěrnosti údajů

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

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

—

Svazek periodika

45

Číslo periodika v rámci svazku

19

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

8563-8571

Kód UT WoS článku

000644392600001

EID výsledku v databázi Scopus

2-s2.0-85106174573