ChemInform Abstract: A Crown Ether Tetrathiafulvalene Cage
J. BECHERThomas K. HansenN. MalhotraGustav BojesenS. BOEWADTK. Sukumar VarmaB. GirmayJeremy KilburnA. E. Underhill
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Abstract (V) (which shows two reversible one‐electron oxidation waves at +0.41 and +0.73 V in cyclic voltammetry vs.Keywords:
Cage
Tetrathiafulvalene
M. Brøndsted Nielsen and J. Becher, Chem. Commun., 1998, 475 DOI: 10.1039/A707026H
Tetrathiafulvalene
Acceptor
Electron acceptor
Electron donor
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Abstract The crystal structure of the KSCN complex of 1,5‐bis(N‐monoaza‐15‐crown‐5)‐3‐oxapentane (BOA15C5) is investigated and discussed in detail.
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Abstract Three types of bis(crown ether) dyes bearing one or two azophenol units were synthesized, which may be expected to show different cation-complexing properties from the corresponding monocyclic crown ether dyes. The extraction of alkali and alkaline-earth metal salts with the crown ether dyes suggested that some cooperative action of the two adjacent crown ether moieties of the bis(crown ether)s occurs on complexing metal cations, although the bis(crown ether) effect is not very remarkable.
Alkaline earth metal
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A simple one-step procedure is reported for the preparation of tetrakis(benzoylthio)tetrathiafulvalene (2) using octacarbonyldicobalt. The crystal structure of 2 is discussed and the preparation of some charge-transfer salts of 2 and their electrical conductivity has been determined. The use of 2 as a synthon for functionalised bis(ethylenedithio)tetrathiafulvalene derivatives is described.
Tetrathiafulvalene
Synthon
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Abstract Structurally related dibenzo‐16‐crown‐5 lariat ethers with pendant ester and ether groups are prepared. Structural variations within the series of alkyl lariat ether esters include changes in the O‐alkyl group, attachment site and nature of the lipophilic group, and length of the spacer, which connects the ester group to the polyether framework. Also synthesized are bis(crown ether) diesters with two dibenzo‐16‐crown‐5 or two dicyclohexano‐16‐crown‐5 units and two ester groups connected to each other by a linker of varying length. Synthetic strategies for the preparation of these lariat ethers with pendant ester‐ and ether‐containing side arms are described.
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Williamson ether synthesis
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New blood for crown ether chemistry! Beside the well-known organocrown ether sandwich complexes 1 there now exist topologically equivalent metallacrown ether complexes 2. These metallasandwich complexes are generated in a one-pot reaction by spontanous self-assembly and in one case have been unambiguously characterized by a crystallographic structure analysis.
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1,3,5,8-Tetrathianaphthalene (2, TTN; 1,4,5,8-tetrathiatetralin) has been synthesized in one step from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione (1) and cis-dichloroethylene in high yield. TTN (2) is readily converted into tetrathiafulvalene (2, TTF) upon tetralithiation or bis(ethylenedithio)tetrathiafulvalene (4, BEDT-TTF) upon tetralithiation, sulfur insertion into the carbon-lithium bond pairs and subsequent capping of the reactive intermediate with 1,2-dibromoethane. The rearrangement of TTN allows for a facile synthesis of TTF and a novel non-coupling route to BEDT-TTF.
Tetrathiafulvalene
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Abstract Based on considerations of membrane activity, a DDT analogue containing crown ether moieties has been conceived and prepared. The preparation of the compound represents a novel route for obtaining crown ether derivatives.
Diphenyl ether
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Williamson ether synthesis
Characterization
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