Chemistry of 2,14-Dithiacalix[4]arene: Searching for the Missing Fifth Conformer

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43923435" target="_blank" >RIV/60461373:22310/21:43923435 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/21:43923435
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c01173" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c01173</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.1c01173" target="_blank" >10.1021/acs.joc.1c01173</a>

Result language
angličtina
Original language name
Chemistry of 2,14-Dithiacalix[4]arene: Searching for the Missing Fifth Conformer
Original language description
Contrary to theoretical predictions, direct alkylation of 2,14-dithiacalix[4]arene provides only four out of five basic conformers (atropisomers). To prepare the missing 1,2 (C)-alternate conformer, the indirect alkylation strategy was applied using 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane as a protective agent. As proved by the combination of NMR and X-ray crystallography, the position of the disiloxane bridge on the macrocycle is not fixed and can be changed under basic conditions, representing thus so far unknown rearrangement of the siloxane moiety. The subsequent dialkylation/deprotection and dialkylation enabled the synthesis of the last missing conformer. As demonstrated by several examples, the mixed-bridge macrocycle (with both CH2 and S bridging units) enables preparation of unusual conformers or substitution patterns, which are difficult to obtain, if at all, in classical calixarene chemistry. This feature makes 2,14-dithiacalix[4]arene a very promising candidate for the role of molecular scaffold or platform in various supramolecular applications.
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
Result was created during the realization of more than one project. More information in the Projects tab.
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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