First synthesis of adamantylated thiacalix[4]arenes

Shokova, E. A.; Тафеенко, В. А.; Ковалев, В. В.

doi:10.1016/s0040-4039(02)00977-2

Cited by 40 publications

(33 citation statements)

References 23 publications

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“…Tetrathiacalix [4]arenes 1 are novel widely developed members of the calixarene family in which the methylene bridges are replaced by sulfur atoms. The introduction of a heteroatom as a bridge provides an additional opportunity to tune the ring size, conformational and binding properties of a macrocycle.…”

Section: Introductionmentioning

confidence: 99%

“…Since the starting p-R-thiacalix [4]arenes (1, R = tert-butyl, tert-octyl, 1-adamantyl or phenyl) [2][3][4][5] are accessible now in multi-gram scale, these macrocycles have sparked a great deal of interest as building blocks in the synthesis of more complicated systems. The regioselective alkylation and acylation of the lower rim hydroxyls of the classical calix [4]arenes have become important synthetic tools for the construction of a great variety of synthetic receptors. Unfortunately, similar regioselective reactions cannot be performed on the thiacalix [4]arene platform to the same extent of efficacy.…”

Section: Introductionmentioning

confidence: 99%

“…The regioselective alkylation and acylation of the lower rim hydroxyls of the classical calix [4]arenes have become important synthetic tools for the construction of a great variety of synthetic receptors. Unfortunately, similar regioselective reactions cannot be performed on the thiacalix [4]arene platform to the same extent of efficacy. The lower apparent differences in the OH acidities 6 of the thiacalix [4]arenes as compared to the classical ones prevents the regio-and stereoselective partial O-alkylation and acylation of thiacalix [4]arenes .…”

Section: Introductionmentioning

confidence: 99%

“…Unfortunately, similar regioselective reactions cannot be performed on the thiacalix [4]arene platform to the same extent of efficacy. The lower apparent differences in the OH acidities 6 of the thiacalix [4]arenes as compared to the classical ones prevents the regio-and stereoselective partial O-alkylation and acylation of thiacalix [4]arenes . As a result, the relatively easy formation of tetralkylated thiacalix [4] 12 have been proposed to overcome the problems encountered in basemediated alkylations.…”

Section: Introductionmentioning

confidence: 99%

“…

AbstractThe selective monocyanomethylation of p-R-thiacalix [4]arenes (R = H, tert-Bu) with chloroacetonitrile in the presence of Na 2 CO 3 in DMF is described.

…”

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confidence: 99%

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Monocyanomethylated thiacalix[4]arenes: synthesis and lower rim modification

Ковалев¹,

Khomich²,

Shokova³

et al. 2008

Arkivoc

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…

AbstractThe selective monocyanomethylation of p-R-thiacalix [4]arenes (R = H, tert-Bu) with chloroacetonitrile in the presence of Na 2 CO 3 in DMF is described.

…”

mentioning

confidence: 99%

See 3 more Smart Citations

Monocyanomethylated thiacalix[4]arenes: synthesis and lower rim modification

Ковалев¹,

Khomich²,

Shokova³

et al. 2008

Arkivoc

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Diamondoid Molecules

Mansoori¹

2007

Advances in Chemical Physics

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Diamondoids have been of great interest in recent years due to their role in nanotechnology, drug-delivery and medicine. In this review paper we introduce at first the cage nature of diamondoid molecules (polymantanes, adamantologues), the variety of their crystalline lattice structures, the nature of their structural isomers, their stereoisomers, and their other molecular specificities are presented. The carbon-carbon framework of diamondoids constitutes the fundamental repeating unit in the diamond lattice structure. It is demonstrated that diamondoids are very stable compounds.The unique physicochemical properties of diamondoids due to their exceptional atomic arrangements including their melting points, molar enthalpies, molar entropies, molar heat capacities, vapor pressures and other phase transitions and solubilities data are reported and analyzed.The Lewis acid-catalyzed rearrangement of hydrocarbons to synthesize lower diamondoids is presented and its limitations for the synthesis of higher diamondoids are discussed.The natural occurrence of diamondoids in petroleum fluids and how they come to be present in such fluids is introduced. Field experiences of phase transitions and depositions as well as techniques for separation, detection and measurement of diamondoids from petroleum fluids is presented and discussed..It is demonstrated that due to their six or more linking groups diamondoids have found major applications as templates and as molecular building blocks in polymers synthesis, nanotechnology, drug delivery, drug targeting, DNA directed assembly, DNA-amino acid nanostructure formation and in host-guest chemistry. ________________________________________ (*) E-Mail: mansoori@uic.edu. 2 Molecular Structure of DiamondoidsDiamondoid molecules are cage-like, ultra-stable, saturated hydrocarbons. These molecules are ringed compounds, which have a diamond-like structure consisting of a number of six-member carbon rings fused together (see Figure 1). More explicitly, they consist of repeating units of ten carbon atoms forming a tetra-cyclic cage system [1-3]. They are called "diamondoid" because their carbon-carbon framework constitutes the fundamental repeating unit in the diamond lattice structure. This structure was first determined in 1913 by Bragg and Bragg [4] using X-ray diffraction analysis.The first and simplest member of the diamondoids group, adamantane, is a tricyclic saturated hydrocarbon (tricyclo[3.3.1.1]decane). Adamantane is followed by its polymantane homologues (adamantologues): diamantane, tria-, tetra-, penta-and hexamantane. Figure 1, illustrate the smaller diamondoid molecules, with the general chemical formula C 4n+6 H 4n+12 : adamantane (C 10 H 16 ), diamantane (C 14 H 20 ), and triamantane (C 18 H 24 ),.. These lower adamantologues, each has only one isomer.Depending on the spatial arrangement of the adamantane units, higher polymantanes (n≥4) can have several isomers and non-isomeric equivalents. There are three possible tetramantanes all of which are isomeric. They are depicte...

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