Molecular structures of the free and η1-coordinated triphenylstannane dithiobenzylester, (C6H5)3SnCS2CH2C6H5

Hiller, W.; Kunze, U.; Tischer, Reinhard

doi:10.1016/s0020-1693(00)84371-6

Cited by 5 publications

(7 citation statements)

References 31 publications

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“…A limited number of stannanedithioesters have been reported in the literature [8][9][10][11][12][13].…”

Section: Resultsmentioning

confidence: 99%

“…Finally, the only described trialkyltin dithioester possessed a tricyclohexylstannyl group [9]. This class of compounds was studied in the eighties but not to a great extent, and only two crystal structures were determined [8,13], namely for methyl and benzyl triphenylstannanecarbodithioates. In this study we describe a new access to this type of compounds.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds exist in two different space groups, but the inequality in crystalline system does not generate any significant differences in the geometry. Selected parameters of planar SnCS 2 unit for compounds 5 and 6 and previously described methyl [8] and benzyl [13] triphenylstannyldithioesters are collected in Table 2. Almost all the key bond lengths and angles are similar in the listed compounds.…”

Section: Resultsmentioning

confidence: 99%

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Unexpected fragmentation of bis(triarylstannanethiocarbonyl)disulfides, formation and X-ray structure of triarylstannyl triarylstannanecarbodithioates

et al. 2015

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Keywords: stannanecarbodithioate, intramolecular nucleophilic substitution, X-ray analysis, intramolecular interaction.The synthesis of bis(triarylstannanethiocarbonyl)disulfides was attempted by oxidation of lithium triarylstannanecarbodithioates with molecular iodine. Unexpectedly, the desired compounds are highly unstable and undergo subsequent fragmentation giving triarylstannyl triarylstannanecarbodithioates. The proposed mechanism for this transformation assumes intramolecular nucleophilic substitution with formation of six-membered ring transition complex, stabilized by interaction between tin and thiocarbonyl sulfur atom. Obtained compounds were identified by mass-spectrometry and NMR spectroscopies, and their structures were analyzed by X-ray diffraction. These molecules show the existence of intramolecular non-bonding interactions between the sulfur atoms of the thiocarbonyl moieties and tin atoms. These interactions reflect the tin -sulfur affinity and are the main driving force in the fragmentation of bis(triphenylstannanethiocarbonyl)disulfides. ________________________________________________________________________________

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“…A limited number of stannanedithioesters have been reported in the literature [8][9][10][11][12][13].…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Unexpected fragmentation of bis(triarylstannanethiocarbonyl)disulfides, formation and X-ray structure of triarylstannyl triarylstannanecarbodithioates

et al. 2015

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“…There are nineteen derivatives which contain tin and tungsten atoms together [57,68,[79][80][81][82][83][84][85][86][87][88][89][90][91][92]. In fifteen of these the tin and tungsten have a direct bond with bond distances ranging from 270.…”

Section: Figure 2 Structure Of [Chbusn^-v-s2cpcy 3 )([I-cimo(co)2(pcmentioning

confidence: 99%

“…6(1) pm [80] to 283. The tin stereochemistry varies from trigonal-planar [83,93] [57,[79][80][81][82][84][85][86][88][89][90][91][92], trigonal-bipyramidal [81,82,87] to pseudo-octahedral [68], The tungsten environments include pseudo-octahedral [57,[81][82][83]86,87], seven-coordinate [84,85,89], semi-sandwiched [68,88,90] and sandwich [80]. The tin stereochemistry varies from trigonal-planar [83,93] [57,[79][80][81][82][84][85][86][88][89][90][91][92], trigonal-bipyramidal [81,…”

Section: Figure 2 Structure Of [Chbusn^-v-s2cpcy 3 )([I-cimo(co)2(pcmentioning

confidence: 99%

Heterometallic Tin Compounds: Classification and Analysis of Crystallographic and Structural Data: Part 1. Dimeric Derivatives

Holloway¹,

Melnı́k²

2001

Main Group Metal Chemistry

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This review covers the crystallographic data for dimeric tin compounds with one other metal atom centre, following the pattern of the previous reviews on tin coordination and organometallic compounds. Over two hundred and forty such derivatives have been characterised, twenty three with a non-transition heterometal atom, one with an actinide metal and the rest with a transition metal atom. The predominant geometries of the tin and the heteroatom are discussed along with the relationships between atom size, bond distances and bond angles. The occurrences of direct metal-metal bonds, and examples of isomerism are illustrated CONTENTS 0. ABBREVIATIONS 1. DIMERIC COMPOUNDS 2.1 Α-Group (Non-Transition) MetalsCrystallographic and structural data for some twenty three tin heterometallic compounds with sub-group A. or non-transition metals, are summarised in Table 1. These are listed in their Periodic Group order, with the typical metals of each group first, and then the Sn-M distance. The first eight derivatives contain tin with lithium [6][7][8][9][10][11][12][13], with the tin in the +2 oxidation state and lithium in its usual +1 oxidation state. The shortest Sn-Li bond 136 Brought to you by | Purdue University Libraries Authenticated Download Date | 6/11/15 11:28 PM Main Group Metal Chemistry Vol. 24, Nr. 3, 2001 distance is found in a yellow derivative [6] at 277.6(4) pm. Here, three Ph(Bu')CN ligands bridge the lithium and tin atoms via their Ν atoms, with Sn-N-Li bridge angles of 81,5( 1A slightly longer Sn-Li distance of 278.4(4) pm is found in a cyclometalated dimer [7] leid together by bridging Ο atoms of three 2,6diphenylphenoxide ligands, with mean Sn-O-Li bridge angles of 84.5(2)°.Two crystallographically independent molecules within the asymmetric units of Ph3SnLi(pmdeta) [8] differ essentially by degree of distortion. While the Sn(II) atom is coordinated by three phenyl groups, the Li(I) atom utilises the tridentate pmdeta moiety. Four coordination is accomplished by each metal via a direct Sn-Li bond of 286.1(7) and 288.2(7) pm in the respective distortion isomers. Another colourless derivative [9] also contains two crystallographically independent molecules. A direct Sn-Li bond of 289(4) and 297(5) pm, respectively, hold together the N3Sn and LiCb moieties.A lithium atom in the next derivative [ 10] ties two amido groups together to generate an N-donor arrangement which forms part of the N3Sn pyramid, one corner of which is the Sn(II) atom. The structure of a red derivative [11] involves a {(Me3Si)3}2Sn unit coordinated to a LiCl(thf)3 moiety via a chlorine bridge. The tricoordinated Sn(II) atom is also at one corner of a pyramid. A tricoordinated tin atom is also found in a metallocyclic arrangement [12] of a four membered (Sn-P-Li-P) ring with average Sn-P-Li angles of 89.5(7)°.The Sn centre in a sandwich style complex [13] is attached to two distorted η-cp ligands and the planar Ν atom of a (Me3Si)2N group, as seen in Figure 1. The tin atom has a distorted pyramidal geometry, and the cp(Y) ligand h...

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Alkyl Triarylstannanecarbodithioates: Synthesis, Crystal Structures, and Efficiency in RAFT Polymerization

Kulai

Saffon‐Merceron

Voitenko

et al. 2017

Chemistry A European J

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Eight alkyl triarylstannanecarbodithioates were synthesized starting from the corresponding triarylstannyl chlorides. They were fully characterized by IR and H, C, and Sn NMR spectroscopy and mass spectrometry. Their solid-state structures and geometric parameters were determined and compared to those of other classes of thiocarbonylthio compounds. These new organotin derivatives are efficient reversible chain-transfer agents for reversible addition-fragmentation chain transfer (RAFT) polymerization of styrene (St) and n-butyl acrylate (BA), with controlled number-average molecular weights and narrow dispersities (Ð<1.3). In some cases, loss of control of the polymerization was evidenced and supported by the observation of side products by Sn NMR spectroscopy. This phenomenon was attributed to the thermal instability of the Sn-RAFT terminal group.

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Molecular structures of the free and η1-coordinated triphenylstannane dithiobenzylester, (C6H5)3SnCS2CH2C6H5

Cited by 5 publications

References 31 publications

Unexpected fragmentation of bis(triarylstannanethiocarbonyl)disulfides, formation and X-ray structure of triarylstannyl triarylstannanecarbodithioates

Unexpected fragmentation of bis(triarylstannanethiocarbonyl)disulfides, formation and X-ray structure of triarylstannyl triarylstannanecarbodithioates

Heterometallic Tin Compounds: Classification and Analysis of Crystallographic and Structural Data: Part 1. Dimeric Derivatives

Alkyl Triarylstannanecarbodithioates: Synthesis, Crystal Structures, and Efficiency in RAFT Polymerization

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