Pinacolophanes as versatile precursor for the practical synthesis of tolanophanes

Darabi, Hossein Reza; Rastgar, Saeed; Aghapoor, Kioumars; Mohsenzadeh, Farshid

doi:10.1007/s00706-017-2125-3

Cited by 2 publications

(2 citation statements)

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“…The bis-thiosemicarbazone ligands with flexible and rigid spacers were obtained in two or three steps according to reported procedures. 49–52 They were characterized by ESI-MS, FT-IR and NMR spectroscopy confirming their structures and were used without further purification.…”

Section: Resultsmentioning

confidence: 99%

“…The ligands H 2 L 1 -H 2 L 3 have been obtained in two steps (Scheme 3): (i) synthesis of 2-[4-(2-formylphenoxy)butoxy]benzaldehyde 49 and (ii) condensation of the dialdehyde 2,2′-[butane-1,4-diylbis(oxy)]dibenzaldehyde following general procedures. 45,50 The mixture of 596 mg (2 mmol) of 2-[4-(2-formylphenoxy) butoxy]benzaldehyde, 524 mg or 780 mg (4 mmol) N-allyl or N-2,3-dimethylphenyl-thiosemicarbazide and 5 drops of glacial acetic acid as a catalyst, in methanol (50 mL) was refluxed for 6 hours.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

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Tuning the nuclearity of [Mo₂O₂S₂]²⁺-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

et al. 2023

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Section: Resultsmentioning

confidence: 99%

Section: Synthetic Proceduresmentioning

confidence: 99%

Tuning the nuclearity of [Mo₂O₂S₂]²⁺-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

et al. 2023

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Enhanced Activity in the Tosylation of Tolanophanes via Supramolecular HgCl2 Recognition

et al. 2020

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The ‘self-activation’ of host molecules via the incorporation of a guest has received considerable attention in supramolecular catalysis. Here, we demonstrate how HgCl2 effects the tosylation rate of tolanophanes (1a–c: n=2−4) with different alkyl chain lengths. Among these substrates, 1a has the highest strain in sp carbons and, therefore, is active even without assistance of HgCl2. In contrast, 1c is inert and needs to be activated in the presence of HgCl2. Therefore, the averaged reaction rate is in the following order: 1c>1b>1a, confirming the role of the supramolecular cavity of 1 over the strain of alkyne bonds. Ab initio calculations are consistent with the experimentally derived reactivity, supporting our size-fitting hypothesis. In contrast, acyclic analogues showed lower activity in the presence of HgCl2 to confirm the effect of the ring cavity. To gain more information, the HgCl2 complexation of 1b was examined by using 1H NMR and UV-vis spectroscopies. All products 5 are new and well characterized. The hydration of isomeric mixtures of 5b,c gave the corresponding single products 4b,c.

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Pinacolophanes as versatile precursor for the practical synthesis of tolanophanes

Cited by 2 publications

References 23 publications

Tuning the nuclearity of [Mo₂O₂S₂]²⁺-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

Tuning the nuclearity of [Mo₂O₂S₂]²⁺-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

Enhanced Activity in the Tosylation of Tolanophanes via Supramolecular HgCl2 Recognition

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Pinacolophanes as versatile precursor for the practical synthesis of tolanophanes

Cited by 2 publications

References 23 publications

Tuning the nuclearity of [Mo2O2S2]2+-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

Tuning the nuclearity of [Mo2O2S2]2+-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

Enhanced Activity in the Tosylation of Tolanophanes via Supramolecular HgCl2 Recognition

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Tuning the nuclearity of [Mo₂O₂S₂]²⁺-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands

Tuning the nuclearity of [Mo₂O₂S₂]²⁺-based assemblies by playing with the degree of flexibility of bis-thiosemicarbazone ligands