Synthesis of 2,8-dithiacalix[4]arene based on fragment condensation
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43923407" target="_blank" >RIV/60461373:22310/21:43923407 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/21:43923407
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0040403921001088" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0040403921001088</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tetlet.2021.152924" target="_blank" >10.1016/j.tetlet.2021.152924</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of 2,8-dithiacalix[4]arene based on fragment condensation
Original language description
A simple synthesis of 2,8-dithiacalix[4]arene 6 comprising two types of bridges (-CH2- and -S-) within a basic macrocyclic skeleton is reported. By optimizing the method we were able to replace 4 steps of the original stepwise procedure with one step in >50% yield, allowing multigram synthesis of the macrocycle. As documented by the H-1 NMR study, the presence of a mixed-bridge system enables direct observation of the so-called flip-flop rearrangement of the hydrogen bond array on the lower rim of the macrocycle. Moreover, the preliminary results showed quite unusual conformational outcomes for the alkylation reactions. The structure of the alkylated macrocycle was confirmed by single crystal X-ray analysis.
Czech name
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Czech description
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Classification
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
Result continuities
Project
<a href="/en/project/GA19-08273S" target="_blank" >GA19-08273S: Calixarene derivatives with mixed bridging units</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron Letters
ISSN
0040-4039
e-ISSN
—
Volume of the periodical
69
Issue of the periodical within the volume
13.dubna 2021
Country of publishing house
GB - UNITED KINGDOM
Number of pages
6
Pages from-to
152924
UT code for WoS article
000636319400001
EID of the result in the Scopus database
2-s2.0-85102438241