- A utility for organoleads: Selective alkyl and aryl group transfer to tin
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Me4Pb and Ph4Pb readily transfer methyl or phenyl groups to an equivalent molar ratio of tin(iv) chlorides in the order SnCl4 > MeSnCl3 > Me2SnCl2 > Me3SnCl, often in a selective manner. Me3PbCl and Ph3PbCl specifically transfer a single methyl/phenyl group under the same reaction conditions to produce recovered yields in >75%. Specific transfer of 2 methyl groups from PbMe4 can be achieved at elevated temperatures and/or a 2:1 molar ratio Pb:Sn.
- Arias-Ugarte, Renzo N.,Pannell, Keith H.
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p. 1703 - 1708
(2018/02/09)
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- A sterically congested aryltrimethylstannane - Synthesis, reactivity, transmetalation and CH-π interaction
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The synthesis of a novel sterically congested tetraorganotin compound, (4-tert-butyl-2,6-dimesitylphenyl)trimethylstannane (1), is reported and its reactivity with special focus on transmetalation studied. The reaction of compound 1 with reagents such as HgCl2, BiCl3 and HOTf gave (4-tert-butyl-2,6-dimesitylphenyl)dimethyltin chloride (2) and (4-tert-butyl-2,6-dimesitylphenyl)dimethyltin triflate (3), respectively, as a result of selective tin-methyl bond cleavage. Less bulky aryltrimethyltin derivatives react with BiCl3 to give both tin-methyl and tin-aryl bond cleavage. Hydrolysis of compound 3 proceeds slowly to give bis-(4-tert-butyl-2,6-dimesitylphenyl)dimethyl stannoxane (5) via the intermediate (4-tert-butyl-2,6-dimesitylphenyl)dimethyltin hydroxide (4). All terphenyldimethyltin derivatives that were characterized by single crystal X-ray diffraction analysis show C-H?π interactions. Based on these results, the optimum C-H?π distance (C?centroidaryl distance) is suggested to be in the range 3.4 and 3.5 A?.
- Mehring, Michael,Nolde, Christof,Schürmann, Markus
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p. 745 - 752
(2009/05/30)
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- PROCESS FOR THE PREPARATION OF HYDROCARBYL HALIDES
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Described is a process for the preparation of hydrocarbyl metal halides, such as alkyl tin chlorides, in which a reaction between the metal in its metallic state and a hydrocarbyl halide is catalyzed by a dihydrocarbyl sulfoxide or a dihydrocarbyl formamide in the presence of a hydrocarbyl metal halide and wherein the pressure of the reaction vessel is varied during the reaction.
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Page/Page column 13; 15
(2008/06/13)
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- Platinum- and palladium-catalysed Kocheshkov redistribution of dialkyltin dichlorides or tetraalkyltins with tin tetrachloride
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The Kocheshkov redistribution reaction of tetraalkyltin or dialkyltin dichlorides with tin tetrachloride is effectively catalysed by platinum(II) or palladium(II) phosphine complexes, yielding alkyltin trichlorides in high yield and with high selectivity.
- Thoonen,Deelman,Van Koten
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p. 1840 - 1841
(2007/10/03)
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- Synthesis and reactivity of stannyloligosilanes, I. Stannyloligosilane chains containing SiMe2 moieties
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Stannyloligosilanes 1 and 2 with terminal organotin groups are available by reacting alkali metal tri-or diorganostannides with α,ω-dichloro-or difluorosilanes, or by treatment of organochlorostannanes with α,ω-difluorosilanes in the presence of magnesium. Attempts to functionalize the triorganotin derivatives 2 by halogenation reagents did not result in the halogen compounds 5; instead cleavage of silicon-tin bonds is observed. In contrast, reactions of the hydridotin derivatives 1 with CHX3 (X = Cl, Br) lead to the quantitative formation of the bis(chloro-or bromostannyl)oligosilanes 5. All compounds were characterized by NMR, IR, MS and elemental analysis. In addition, the triorganotin compound 2i and the hydridotin species 1b have been characterized by X-ray crystallography.
- Uhlig, Frank,Kayser, Christian,Klassen, Ralph,Hermann, Uwe,Brecker, Lothar,Schürmann, Markus,Ruhland-Senge, Karin,Englich, Ulrich
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p. 278 - 287
(2007/10/03)
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- Coordination chemistry of group 14 metalloles. 3. Synthesis and reactivity of 1,1-dimethyl- and 1,1,3,4-tetramethylsilole and 1,1,3,4-tetramethylgermole complexes
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Silacyclopentadienes and germacyclopentadienes (metalloles) without phenyl substituents are effective ligands for transition-metal complexes. Direct displacement of carbonyl ligands from Fe2(CO)9, Ru3(CO)12, or
- Burns, Gary T.,Colomer, Ernest,Corriu, Robert J. P.,Lheureux, Marc,Dubac, Jacques,Laporterie, André,Iloughmane, Hafida
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p. 1398 - 1406
(2008/10/08)
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- SOME REACTIONS OF TRIS(TRIMETHYLSTANNYL)-AND TETRAKIS(TRIMETHYLSTANNYL)-METHANE
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With a variety of electrophilic reagents reaction occurs exclusively at the CH3-Sn bonds of 4C and 3CH.While the inner Sn-C bonds remain intact, methyl groups may be progressively cleaved off, one from each of the trimethylstannyl groups; in the case of bromine a second Me group may be cleaved from each of the SnMe2Br groups.The various products were identified by 1H, 13C and 119Sn MNR spectroscopy.
- Hawker, Darryl W.,Wells, Peter R.
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- THE ULTRAVIOLET DEGRADATION OF THE METHYLTIN CHLORIDES IN CARBON TETRACHLORIDE AND WATER
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The ultraviolet degradation of the methyltin chlorides in carbon tetrachloride and water has been quantitatively studied by 1H NMR spectroscopy.In the organic solvent trimethyltin chloride degraded to an inorganic tin species, via di- and mono-methyltin intermediates; in water, a monomethyltin derivative was not observed.The ultraviolet breakdown of dimethyltin dichloride and monomethyltin trichloride in these solvents was also studied, and the approximate relative rates of degradation were established.
- Blunden, Stephen J.
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p. 149 - 160
(2007/10/02)
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- Process for preparing monohydrocarbyltin trihalides
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A process is provided for preparing monohydrocarbyltin trihalides, RSnX3, wherein R is an alkyl, cycloalkyl, alkaryl, aryl or aralkyl group of 1-24 carbon atoms, and X is a halogen atom by the redistribution reaction between a tetrahydrocarbyltin, R4 Sn, a trihydrocarbyltin halide, R3 SnX, or a dihydrocarbyltin dihalide, R2 SnX2, and a tin tetrahalide, SnX4, in the presence of sulfonium or isothiuronium salts as catalysts.
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- Method for producing monoalkyl-tin-trihalides
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Monoalkyl-tin-trihalides are prepared in a high yield by a method in which a stannous halide reacts with an alkyl halide in an organic solvent in the presence of a catalytic substance selected from the group consisting of magnesium, iodine, bromine, Grignard reagents and a mixture of two or more of the above-mentioned substances, the organic material being selected from liquid alcohols, tetrahydrofuran, liquid organic acids, liquid esters of organic acids, liquid ketones, liquid hydrocarbons and mixtures of two or more of the above-mentioned compounds, and the resultant monoalkyl-tin-trihalide is isolated from the reaction mixture.
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