Sulfonate-bonded tin complexes for the production of diphenyl carbonate

Lee, Hyunjoo; Bae, Jangho; Kwon, Ohsuk; Kim, Sung Joon; Lee, Sang Deuk; Kim, Hoon Sik

doi:10.1016/j.jorganchem.2004.02.039

Cited by 48 publications

(25 citation statements)

References 11 publications

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“…2b) coordination of organotin and carboxyl group. To ascertain the block ratio, a few drops of trifluoroacetic acid were added into the NMR tube, with the purpose of destroying the self-assembly behavior by dissociating organotin from the polymer chain, based on the substitution reaction between organotin carboxylate and Bronsted acid [49][50][51][52] . As a result, the solution of block copolymer in CDCl 3 became transparent immediately and the singal of -CH 2 CH 2 CH 2 CH 3 on the organotin block appeared in 1 H-NMR.…”

Section: Resultsmentioning

confidence: 99%

“…To confirm that the self-assembly driving force comes from the coordination between tin and carboxyl group, we attempted to remove off the organotin unit from the block copolymer. Namely, the block copolymer was refluxed for 24 h in acetic acid instead of trifluoroacetic acid to avoid the possible acidolysis of PMMA block in strong acid [49][50][51][52] . White powder was obtained after precipitating reaction mixture in petroleum ether.…”

Section: Resultsmentioning

confidence: 99%

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Morphological studies on Sn-O coordination driving self-assembly of well-defined organotin-containing block copolymers

et al. 2014

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A tin-oxygen coordination driving self-assembly was developed in the block copolymers containing organotin, which were prepared by the radical addition-fraction transfer (RAFT) method and characterized by the gel-permeation chromatography (GPC) and 1 H-NMR. And the self-assemblies of these block copolymers with various chain length ratios in the different concentrations in CHCl 3 were stable according to the results of DLS and TEM. Additionally, it was also given an insight investigation on the regulation of self-assembly of the block copolymers by adding dibutyltin dichloride and a possible mechanism was proposed.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Morphological studies on Sn-O coordination driving self-assembly of well-defined organotin-containing block copolymers

et al. 2014

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Section: Reactivity Of ((Phch 2 ) 2 Sno) 6 [((Phch 2 ) 2 Snoh) 2 (Co mentioning

confidence: 99%

“…Recently, continuing our investigation in this domain, we published the preparation of an unexpected trifluoromethanesulfonato di-n-butylin(IV)-based supramolecular 2D framework induced by phenazine [15f]. In addition to the structural interest, organotin(IV) trifluoromethanesulfonate complexes are active in homogeneous catalysis as Lewis acids for organic reactions such as the Mukaiyama aldol reaction [25], the Robinson annulation [26], the acetylation of alcohols [27], and the transesterification of dimethyl carbonate with phenol [28].The addition of trifluoromethanesulfonic acid to a suspension of 2 in acetonitrile gave a clear solution after stirring for 2 h at r. t. Removal of solvent in vacuo and washing of the tin-based residue with dichloromethane yielded a homogeneous colorless powder. Interestingly, the 119 Sn{ 1 H} NMR spectrum of the powder dissolved in CD 3 CN shows an upfield signal located at δ = −474.2 ppm suggesting the presence of hexacoordinated tin atoms.…”

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confidence: 99%

Unprecedented Hexa- and Undecanuclear Frameworks of Two New Tin(IV) Oxo Clusters Resulting from Partial Debenzylation Reactions

Plasseraud

Cattey

Richard

2010

Zeitschrift Für Naturforschung B

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A new and facile synthetic route to the known neutral cluster ((PhCH 2 ) 2 SnO) 6 [((PhCH 2 ) 2 SnOH) 2 -(CO 3 )] 2 (2) as well as its reactivity toward trifluoromethanesulfonic acid (HO 3 SCF 3 , TfOH) are reported. The solid-state structure of the new solvate 2·6C 7 H 8 has been determined by single-crystal X-ray diffraction. The core of 2 can be described as a pair of coplanar pentanuclear [(PhCH 2 ) 2 SnO] 5 ladders bridged at their ends by two carbonate groups. Successive additions of TfOH to a suspension of 2 in CD 3 CN were monitored by 119 Sn{ 1 H} NMR spectroscopy showing the transformation of the fingerprint of 2 (δ = −244, −246, −306 ppm), via new upfield signals, to a final broad resonance located at δ = −474 ppm. Thereafter, two unprecedented ionic monobenzyltin(IV) oxo clusters, 3 and 4, resulting from a debenzylation reaction and exhibiting unusual hexa-and undecanuclear frameworks, respectively, have been isolated as single crystals. IntroductionOrganotin compounds with Sn-O bonds have a diversity of solid-state structures, from discrete mononuclear compounds to complex clusters and multidimensional networks. Pioneering work in the field of organotin-oxo clusters is attributable to Holmes and Chandrasekhar who in the 1980's discovered several unexpected polynuclear structures and published the first reviews relating to the classification of these compounds [1]. Since then, the inventory of structures has regularly been updated; it reveals a profuse structural diversity [2]. Indeed, on the basis of X-ray crystallographic studies, a great variety of shapes has already been identified for organotin-oxo derivatives which include prismane [3], butterfly [4], ladder [5], O-and Scapped cluster [6], drum [7], cube [8], double cube [9], football cage [10], crown [11], extended cage [12], and coordination polymer types [13]. Moreover, the structural interrelationship between these polynuclear arrangements has been clearly established, highlighting possible mechanisms of interconversion from one form to another [14]. In the past decade, with the growing interest in the assembly of the metal-organic frameworks 0932-0776 / 10 / 1100-1293 $ 06.00 c 2010 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com (MOFs), organotin-oxo moieties have also been used as building blocks for designing supramolecular architectures with remarkably large cavities [15]. From a synthetic point of view, organotin assemblies containing Sn-O bonds are generally obtained from the reaction of organotin precursors (such as organotin oxides and hydroxides) in the presence of phosphonic, phosphinic, carboxylic, and sulfonic acids at room temperature or under reflux conditions. Recently, reactions with arylarsonic acids were also explored [16]. In numerous examples, the cleavage of Sn-C bonds leads to the formation of Sn-O bonds [17].Formerly, investigating the direct synthesis of organic carbonates from carbon dioxide and alcohols promoted by organometallic tin(IV) precursors [18], and during recycling experime...

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“…In addition to the structural interest, organotin(IV) trifluoromethanesulfonate complexes are active in homogeneous catalysis as Lewis acids for organic reactions, such as the Mukaiyama aldol reaction [5], the Robinson annulation [6], the acetylation of alcohols [7], and the transesterification of dimethyl carbonate with phenol [8].…”

Section: Introductionmentioning

confidence: 99%

{[(PhCH₂Sn)₁₂(μ₃-O)₁₄(μ-OH)₆](F₃CSO₃)₂}: A New Dodecanuclear Organostannoxane

Plasseraud

Cattey

Richard

2011

Zeitschrift Für Naturforschung B

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The new dodecanuclear organostannoxane {[(PhCH 2 Sn) 12 (µ 3 -O) 14 (µ-OH) 6 ](F 3 CSO 3 ) 2 } (2) has been isolated as single crystals from the reaction of trifluoromethanesulfonic acid (F 3 CSO 3 H) with the decanuclear dibenzyltin(IV)-oxo cluster, [(PhCH 2 ) 2 SnO] 6 {[(PhCH 2 ) 2 SnOH] 2 (CO 3 )} 2 (1), in [D 3 ]acetonitrile, at room temperature. Compound 2 was structurally characterized by X-ray diffraction analysis, multinuclear NMR and IR spectroscopy, mass spectrometry, and thermogravimetry. The structure of 2 can be described as a football cage framework containing twelve tin atoms, exhibiting two distinct coordination geometries, penta-and hexacoordinated respectively, and linked together through µ 3 -O and µ-OH ligands. Resulting from Sn-C bond cleavage, all tin atoms are only connected to one benzyl ligand. Furthermore, two of the three oxygen atoms of each trifluoromethanesulfonate counteranions are involved in hydrogen bonding interactions with bridging µ-OH groups of two distinct Sn 12 cations leading to the propagation of a two-dimensional polymeric network.

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Sulfonate-bonded tin complexes for the production of diphenyl carbonate

Cited by 48 publications

References 11 publications

Morphological studies on Sn-O coordination driving self-assembly of well-defined organotin-containing block copolymers

Morphological studies on Sn-O coordination driving self-assembly of well-defined organotin-containing block copolymers

Unprecedented Hexa- and Undecanuclear Frameworks of Two New Tin(IV) Oxo Clusters Resulting from Partial Debenzylation Reactions

{[(PhCH₂Sn)₁₂(μ₃-O)₁₄(μ-OH)₆](F₃CSO₃)₂}: A New Dodecanuclear Organostannoxane

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Sulfonate-bonded tin complexes for the production of diphenyl carbonate

Cited by 48 publications

References 11 publications

Morphological studies on Sn-O coordination driving self-assembly of well-defined organotin-containing block copolymers

Morphological studies on Sn-O coordination driving self-assembly of well-defined organotin-containing block copolymers

Unprecedented Hexa- and Undecanuclear Frameworks of Two New Tin(IV) Oxo Clusters Resulting from Partial Debenzylation Reactions

{[(PhCH2Sn)12(μ3-O)14(μ-OH)6](F3CSO3)2}: A New Dodecanuclear Organostannoxane

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{[(PhCH₂Sn)₁₂(μ₃-O)₁₄(μ-OH)₆](F₃CSO₃)₂}: A New Dodecanuclear Organostannoxane