Synthesis and structural analysis of mercaptothiacalix[4]arene

Rao, P. Jayaprasad; Hosseini, Mir Wais; Cian, André De; Fischer, Jean

doi:10.1039/a906058h

Cited by 64 publications

(34 citation statements)

References 15 publications

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“…[36] To enhance the complexation ability of the thiacalixarenes, the lower rim hydroxyls were transformed into SH groups. [37] The acylation of 2 with N,N-dimethylcarbamoyl chloride produced the corresponding O-thiocarbamoyl derivative which was thermally converted into the S-carbamoyl derivative (the NewmanϪKwart rearrangement). Deprotection with hydrazine hydrate gave the tetramercaptothiacalix [4]arene 36 in good yield.…”

Section: Lower Rim Derivatization -Shaping Of the Molecular Skeletonmentioning

confidence: 99%

Chemistry of Thiacalixarenes

2004

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Thiacalixarenes — new members of the calixarene family — are very promising molecules with many potential applications in supramolecular chemistry. The presence of four sulfur atoms in the place of methylene groups imparts many novel features and properties to these molecules. This review deals with the chemistry of thiacalixarenes, and by comparision with “classical” calixarenes, emphasizes their differences in reactivity, unusual conformational preferences and modified complexation abilities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Lower Rim Derivatization -Shaping Of the Molecular Skeletonmentioning

confidence: 99%

Chemistry of Thiacalixarenes

2004

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“…[3][4][5][6][7][8][9][10][11][12][13][14][15][16] As synthetic macrocyclic ligands, the calixarenes are somewhat unusual in that the donor sites for metal ion binding are most commonly atoms within pendent substituents rather than within the macrocycle itself. There are parallels here with some naturally occurring "ionophores" [17] but only the relatively recent synthesis of calixarene systems in which sulfur replaces the methylene groups, those of the thiacalixarenes [18][19][20][21] (as well as mercaptothiacalixarenes [22,23] and thiacalixanilines [24,25] ), has provided materials which may be considered comparable to a wide range of macrocycles, both natural (e.g. the porphyrins [26] ) and synthetic, [1] in which macro-…”

Section: Introductionmentioning

confidence: 99%

Systematic Structural Coordination Chemistry ofp‐tert‐Butyltetrathiacalix[4]arene: Main Group Metal Complexes Other Than Those of Group 1

et al. 2010

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In extension of previous work involving structural characterisation of complex salts formed between main group 1 metal ions and p‐tert‐butyltetrathiacalixarene, LH4, the present study encompasses complexes with a wider array of main group 2, 13, 14 metal ions. For group 2, single‐crystal X‐ray structural characterisation of Ca(LH3)2·3dmf (1a), {Ca(LH2)·3dmf}2 (1b), Ba(LH3)2·6dmf (2a) and BaCO3·3Ba(LH3)2·3H2O·3CH3CN·12.25CH2Cl2 (2b) provides models for various coordination units. For group 13, this applies to {Ga(OH)(LH2)·3.5dmf}2 (3), {In(LH)·4EtOH·2CH2Cl2}2 (4a) and {In(OH)(LH2)·3CH2Cl2}4 (4b), and for group 14, to OPb4(LH)2·6dmf·dmso·2H2O (5). Overall, these define mononuclear (1a, 2a), binuclear (1b, 3, 4b) and tetranuclear (2b, 4b, 5) species. The calixarene cavities frequently include solvent molecules, though this capacity is clearly influenced by the nature of the bound metal ion(s) and their binding, as well as the associated impact on the conformation of the calixarene ligand(s).

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“…Reaction of 1 and 2 with simple alkyl halides (RI or RBr, R>C 3 H 7 ) in the presence of base generally gives the tetraalkylated products in 1,3-alternate conformation. [9,10,13] In the case of electrophilic reagents containing n-donor Thiacalix [4]arene's Lower Rim Derivatives groups, [9,10,13,[18][19][20] Easily available by the Newman-Kwart rearrangement tetramercaptothiacalix [4]arene 67 [57] adopting 1,3-alternate conformation [58] undergoes easily base-catalyzed etherification with the formation of carboxyl, pyrazolyl, [31] cyanopropoxy, [59] cyanobenzyloxy [59] and α, β, γ pyridylmethoxy [60] derivatives 6871 (Scheme 3).…”

Section: Synthesis Of Tetrasubstituted Thiacalix[4]arene Derivativesmentioning

confidence: 99%

“…R=t-Bu; Y=H; [57] 68: R=t-Bu; Y=(CH 2 ) n -Pyrazolyl, n=2-4, 1,3-alternate; [31] 69: R=t-Bu; Y=(CH 2 ) 3 CN, 1,3-alternate; [59] 70: R=t-Bu; Y=CH 2 C 6 H 4 CN, 1,3-alternate; [59] 71: R=t-Bu; Y=(CH 2 Py(α,β,γ), 1,3-alternate. [60] Scheme 3.…”

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confidence: 99%