Reactivity of phenoxathiin-based thiacalixarenes towards C -nucleophiles.

Autor: Mamleev K; Department of Organic Chemistry, University of Chemistry and Technology, Prague (UCTP) Technicka 5 166 28 Prague 6 Czech Republic lhotakp@vscht.cz +420-220444288 +420-220445055., Čejka J; Department of Solid State Chemistry, UCTP 166 28 Prague 6 Czech Republic., Eigner V; Department of Solid State Chemistry, UCTP 166 28 Prague 6 Czech Republic., Krupička M; Department of Organic Chemistry, University of Chemistry and Technology, Prague (UCTP) Technicka 5 166 28 Prague 6 Czech Republic lhotakp@vscht.cz +420-220444288 +420-220445055., Dvořáková H; Laboratory of NMR Spectroscopy, UCTP 166 28 Prague 6 Czech Republic., Lhoták P; Department of Organic Chemistry, University of Chemistry and Technology, Prague (UCTP) Technicka 5 166 28 Prague 6 Czech Republic lhotakp@vscht.cz +420-220444288 +420-220445055.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2024 Apr 25; Vol. 14 (19), pp. 13463-13473. Date of Electronic Publication: 2024 Apr 25 (Print Publication: 2024).
DOI: 10.1039/d4ra02524e
Abstrakt: A starting thiacalix[4]arene can be easily transformed into oxidized phenoxathiin-based macrocycles 9 and 9', representing an unusual structural motif in calixarene chemistry. The presence of electron-withdrawing groups (SO 2 , SO) and the considerable internal strain caused by the condensed heterocyclic moiety render these molecules susceptible to nucleophilic attack. The reaction with various organolithium reagents provides a number of different products resulting from the cleavage of either the calixarene skeleton or the phenoxathiin group or both ways simultaneously. This enables the preparation of thiacalixarene analogues with unusual structural features, including systems containing a biphenyl fragment as a part of the macrocyclic skeleton. The above-described transformations, unparalleled in classical calixarene chemistry, clearly demonstrate the synthetic potential of this thiacalixarene subgroup.
Competing Interests: There are no conflicts of interest to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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