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

Result code in 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>
Result on the web
<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>

Result language
angličtina
Original language name
Regio- and stereoselectivity of spirodienone formation in 2,14-dithiacalix[4]arene
Original language description
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.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science 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
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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