Macrocycles incorporating closo- and nido-carbaborane cages: molecular structure of 1,2-(3′-oxapentane-1′,5′-dithiolato-SS′)-1′,2′-dicarba-closo-dodecaborane

Teixidor, Francesç; Romerosa, Antonio; Rius, Jordi; Miravitlles, C.; Casabó, Jaume; Viñas, Clara; Sanchez, Eustaquio

doi:10.1039/dt9900000525

Cited by 40 publications

(9 citation statements)

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“…As a general trend, in the compounds substituted with sulfur the cluster C(1)--C(2) distance is longer than in the unsubstituted compounds or in compounds substituted with silicon or carbon. In the compounds containing two S atoms (Table 1), the C(1)---C(2) distance is 1.858 (5) and 1.826(5)A ) and 1.816(6)A (Teixidor, Romerosa, Rius, Miravitlles, Casab6, Vifias & Sanchez, 1990), whereas in 9,12-isopropylidenedithio-l,2-dicarba-closo-dodecaborane(12), a compound with unsubstituted cluster C atoms, it is only 1.634 (3)A (~ubrtov~., Linek & Ha~ek, 1980). Similarly, when the cluster C atoms are connected directly to silicon the C(1)--C(2) distance is 1.688 (5) A (Kivek~is, Romerosa & Vifias, 1994), and when connected to carbon, 1.684 (6)A (Holbrey, Iveson, Lockhart, Tomkinson, Teixidor, Romerosa, Vifias & Rius, 1993).…”

Section: Commentmentioning

confidence: 99%

1-Diphenylphosphino-2-methyl-1,2-dicarba-closo-dodecaborane(12)

Kivekäs¹,

Sillanpää²,

Teixidor³

et al. 1994

Acta Crystallogr C

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Section: Commentmentioning

confidence: 99%

1-Diphenylphosphino-2-methyl-1,2-dicarba-closo-dodecaborane(12)

Kivekäs¹,

Sillanpää²,

Teixidor³

et al. 1994

Acta Crystallogr C

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“…1-oxa-4,7-dithiacyclononane (1,4,7-oxadithionane; [9]aneOS 2 )The first reported synthesis of the macrocyclic polyether[9]aneOS 2 , along with a number of analogues, involved reacting oligoethylene glycol dichloride with a dithiol in EtOH[271].Subsequent refinement of the synthetic methodology involved cyclization of bis(2mercaptoethyl)ether and 1,2-dibromoethane[272], or 1,2-dichloroethane[273], under high dilution conditions in dimethylformamide with caesium carbonate. No X-ray structural data for the ligand itself have been reported; however, the closo-carbaborane, 1,2-(3'-oxapentane-1',5'-dithiolato-SS') -1',2'-dicarba-closo-dodecaborane, incorporating the[9]aneOS 2 moiety, has been structurally characterised (Figure 86)[274].…”

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confidence: 99%

Cyclononanes: The extensive chemistry of fundamentally simple ligands

Gahan

2016

Coordination Chemistry Reviews

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The cyclononane ligands are fundamental examples of the macrocyclic ligand. With three donor atoms in a nine-membered ring they represent the simplest of the macrocyclic class. However, this simplicity is deceptive, for within this class the variations are extensive and perhaps hitherto unrecognized. As well as the relatively familiar 1,4,7-triaza-([9]aneN 3) and 1,4,7-trithia-([9]aneS 3) cyclononanes whole families of cyclononane ligands are known with thioether/nitrogen, nitrogen/oxygen, selenium, tellurium as well as phosphorus and arsenic donors. The chemistry of some of these ligands, for example [9]aneN 2 S, [9]aneNS 2 and [9]aneN 2 O has been reported extensively, and some examples have simply been reported as having been synthesised (for example [9]aneO 2 S and [9]aneO 2 Se) with little other information. This review attempts to introduce the extensive chemistry of what are fundamentally the simplest examples of macrocyclic ligands. 1. Highlights Review of current trends in cyclononane chemistry Diversity of donor groups and transition metal chemistry complexes which arise Significant new synthetic chemistry Significant advances in the applications of cyclononane ligands

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“…Chemical shift values for 11 B-NMR spectra were referenced to external BF 3 ·OEt 2 , those for 1 H-and 13 C{ 1 H}-NMR spectra were referenced to SiMe 4 .…”

Section: Generalmentioning

confidence: 99%

“…After 15 min stirring, SOCl 2 (0.37ml, 5.07mmol) was added and the reaction was left to warm to room temperature overnight. Water (30 ml) was added, dissolving the nascent LiCl, and the ether layer was washed with further water (2 x 30ml) before being isolated and dried over MgSO 4 . Removal of the solvent in vacuo gave a white solid.…”

Section: Attempted Synthesis Ofmentioning

confidence: 99%

“…1,2,3 Derivatives Cb o (SR) 2 of ortho carborane have attracted particular interest, in part in connection with their ligand potential, whether as bidentate chelating ligands, or as components of macrocycles when the substituents R are linked through successive ether or thioether units. 4 Where SR is SH they can be used as precursors to form [closo-RC 2 B 10 H 10 S] -or [closo-C 2 B 10 H 10 S 2 ] 2-anionic residues. 5 They have also been used as precursors from which [nido-C 2 B 9 H 9 (SR) 2 ] 2-anionic residues, offering yet further ligand potential, can be prepared.…”

Section: Introductionmentioning

confidence: 99%

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Preparative and structural studies on sulfur-linked carborane icosahedra: 2-Phenyl-ortho-carboranyl-sulfur systems (2-Ph-1,2-C2B10H10)2X (X=S, S2 or SO), and ortho-carboran-di-yl systems (1,2-C2B10H10Y)2 (Y=S or SO)

et al. 2006

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) 'Preparative and structural studies on sulfur-linked carborane icosahedra: 2-phenyl-ortho-carboranyl-sulfur systems (2-Ph-1,2-C2B10H10)(2)X (X = S, S-2 or SO), and ortho-carboran-di-yl systems (1,2-C2B10H10Y)(2) (Y = S or SO). ', Polyhedron., 25 (2 Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractDetails are reported of the preparation and X-ray structural characterisation of the new compounds (PhCb o ) 2 X, where PhCb o = 12-Ph-1,2-C 2 B 10 H 10 and X = S(1) or SO (3), prepared from PhCb o Li and SCl 2 or SOCl 2 respectively, as well as the known compound with X = S 2 (2). Hydrogen in the presence of palladium/carbon reduced (3) to (1). Features of their structures (exo C-S and cage C-C distances and substituent orientations) are consistent with significant exo S=C dative π-bonding from their sulfur atoms to the cage hypercarbon atoms and weak exo π-bonding from the phenyl groups. Attempts to prepare systems (Cb o Y) 2 , in which two ortho-carboran-di-yl residues Cb o are linked through two bridging units Y (S, SO) are also reported, as are their calculated structures.

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Macrocycles incorporating closo- and nido-carbaborane cages: molecular structure of 1,2-(3′-oxapentane-1′,5′-dithiolato-SS′)-1′,2′-dicarba-closo-dodecaborane

Cited by 40 publications

References 13 publications

1-Diphenylphosphino-2-methyl-1,2-dicarba-closo-dodecaborane(12)

1-Diphenylphosphino-2-methyl-1,2-dicarba-closo-dodecaborane(12)

Cyclononanes: The extensive chemistry of fundamentally simple ligands

Preparative and structural studies on sulfur-linked carborane icosahedra: 2-Phenyl-ortho-carboranyl-sulfur systems (2-Ph-1,2-C2B10H10)2X (X=S, S2 or SO), and ortho-carboran-di-yl systems (1,2-C2B10H10Y)2 (Y=S or SO)

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