1066-44-0Relevant articles and documents
Bromodestannylation reactions of some functionally substituted organotin compounds
Chopa, A. B.,Koll, L. C.,Podesta, J. C.,Mitchell, T. N.
, p. 283 - 296 (1989)
Bromodestannylation reactions are reported for several functional substituted organotin compounds in carbon tetrachloride and acetonitrile as solvents.The reactions in carbon tetrachloride proceed with a high degree of retention of configuration at the carbon involved in the electrophilic substitution, while in a polar solvent there is an increase in the amount of inversion product formed.The electrophilic cleavage in the β-trialkylstannyl esters takes place with a complete reversal of the normal sequence of Sn-C bond cleavage by halogens; this is explained by tin assistance.The configuration of some 3-trialkylstannylpropanenitriles, β-bromonitriles and β-bromoesters are assigned.Full, 1H, 13C and 119Sn NMR data are given.
Mechanisms of the rupture of the carbon-tin bond by halogens II. Free-radical substitution in solution
Boue, S,Gielen, M,Nasielski, J
, p. 461 - 479 (1967)
The experiments describes in this paper show that the light-induced bromodemetallation of tetraalkyltins in chlorobenzene is a free radical substitution on tin, followed by a propagation step: {A figure is presented}. The stabilisation of R? by hyperconjugation seems to be an important factor for the reaction, but there is evidence for the influence of the other three substituents of tin and of the nature of the attacking radical on the reaction mechanism. The relation between the strucutre and the reactivity of tetraalkyltins suggests that the carbon-tin bond is only slightly loosened in the transition state; this agrees with the great reactivity of the Br atom.
Kraus, C. A.,Neal, A. M.
, p. 2403 - 2407 (1929)
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Kraus, C. A.,Bullard, R. H.
, p. 2131 - 2137 (1926)
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Chipperfield, John R.,Ford, James,Hayter, Andy C.,Lee, David J.,Webster, David E.
, (1976)
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Bullpitt,Kitching
, p. 21,27 (1972)
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Okada,T.,Okarawa,R.
, p. 149 - 152 (1973)
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Van Koten et al.
, p. 157,168 (1975)
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Pedley,Skinner
, p. 544,546 (1959)
Charge transfer spectra of organometallic complexes II. Determination of the donor site in trialkyltinhalides
Verdonck, L.,Hoste, S.,Herman, G. G.,Lippens, W.,Kelen, G. P. van der
, (1984)
The charge transfer spectra of several trialkyltiniodide- and bromide-iodine systems are presented.Interpretation of the blue shift, the charge transfer band maximum and the formation constant data leads to the conclusion that, on complexation with iodine
The Mechanism of the Reaction of (Aryloxy)trimethylstannane with Benzyl Bromide giving Aryl Benzyl Ether
Kozuka, Seizi,Kikuchi, Akihiko,Yamaguchi, Shigeru
, p. 307 - 308 (1981)
A kinetic study has been performed for the reaction of (aryloxy)trimethylstannane with benzyl bromide giving aryl benzyl ether and bromotrimethylstannane.Bimolecular nucleophilic attack of the aryloxy-oxygen on the benzyl-carbon has been suggested for the reaction based on the substituent effect.
Santini-Scampucci,C.,Riess,J.G.
, p. 2436 - 2440 (1973)
A catalytic and mechanistic investigation of a PCP pincer palladium complex in the Stille reaction
Olsson, Daniel,Nilsson, Patrik,El Masnaouy, Mostafa,Wendt, Ola F.
, p. 1924 - 1929 (2007/10/03)
In an improved procedure, the complex {2,6-bis[(diphenylphosphino)methyl] benzene}chloropalladium(II) (1) was synthesised as its THF adduct and the structure was determined by X-ray crystallography. The catalytic properties of the derivative {2,6-bis[(diphenylphosphino)methyl]benzene}(trmuoroacetato) palladium(II) (2) was investigated in the Stille reaction. Complex 2 proves to be an excellent catalyst for the C-C cross-coupling between trimethyl phenyl stannane and aryl bromides using a very low catalyst loading (0.1-0.0001%), giving high turnover numbers (TONs) up to 6.9 × 105. A kinetic investigation of the catalytic reaction suggests a heterogeneous colloidal palladium catalyst formed from the PCP Pd(II) pre-catalyst. The Royal Society of Chemistry 2005.
Synthesis of Boron-Halogenated Diborylamines and Diborylhydrazines by Cleavage of Stannazanes
Diemer, Stefan,Noeth, Heinrich,Storch, Wolfgang
, p. 1765 - 1780 (2007/10/03)
The diborylamines R'-N(BRX)2 (3; X=Cl, Br) are obtained by stannazane cleavage of distannylorganylamines R'-N(SnMe3)2 (4) with alkyldihaloboranes RBX2 in a 1:2 molar ratio. The presence of the sterically demanding substituents R and R' also causes carbon-tin bond cleavage, resulting in low yields of 3. However, carbon-tin bond cleavage can be suppressed by the use of bis(dimethylchlorostannyl)organylamines 5 as the nitrogen source for the synthesis of diborylamines. This results in almost quantitative yields of the compounds 3. Treatment of the distannylhydrazines R2N-N(SnMe3)2 (7) with RBX2 in a 1:2 molar ratio leads to the formation of N,N-bis(alkylhaloboryl)hydrazines 8 under mild conditions and in good yield. The molecular structures of 3 and 8 were determined by multinuclear magnetic resonance spectra in solution as well as by X-ray structure analysis in the case of 8d. A typical structural feature of 8d is the intramolecular BN adduct formation. Support for the constitutions of compounds 8c comes from MS fragmentation patterns as well as from IR spectra.
