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Configurational Stability of Triorganostannylamines, ‐Phosphines and ‐Arsines

Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
· DOI :10.1002/bscb.19750841003
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Yves Tondeur6
Estimated H-index: 6
(ULB: Université libre de Bruxelles)
Abstract
Stannylamines, ‐phosphines and ‐arsines are shown to be configurationally stable within the NMR time‐scale, even in the presence of a strong nucleophile. The configurational stability of triorganotin hydrides and the configurational unstability of triorganotin halide has been checked. Copyright © 1975 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
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References10
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#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
#2Hassan Mokhtar-Jamaï (ULB: Université libre de Bruxelles)H-Index: 4
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
#2Stéphane Simon (Vrije Universiteit Brussel)H-Index: 1
Last. Cornelis Hoogzand (Vrije Universiteit Brussel)H-Index: 9
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#2M. De Clercq (ULB: Université libre de Bruxelles)H-Index: 4
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 35
#2Hassan Mokhtar-Jamaï (ULB: Université libre de Bruxelles)H-Index: 4
Abstract Determination of the concentrations of pyridine required to cause coalescence of the neophylic methyl group resonances at 60, 100 and 270 MHz has shown that the racemisation of methylneophyl-t-butyltin chloride or bromide in benzene is of second order in the nucleophile.
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Abstract The NMR study of a large number of mixed tetraorganotins shows that the J vs. Σσ * relationship is invalid, even in the mixed tetraalkyltin series. Malinovski's additivity rule may be used to predict tin-methyl, tin-benzyl and tin-tert-butyl coupling constants.
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The preparation, properties, and reactions of the compounds named in the title are described, with particular reference to the possible participation of (p→d)π components in the bonding between the group IVB and the group VB elements.
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#1K. Jones (University of Manchester)H-Index: 1
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Abstract (Dialkylamino)trialkylstannanes, R 3 Sn-NR′ 2 , are very reactive reagents. With protic species HA, including hydrogen chloride, water, alcohols, ammonia and primary and secondary amines, diphenylphosphine, diphenylarsine, acetylene and monosubstituted acetylenes, cyclopentadiene and indene, they readily eliminate amine R′ 2 NH and afford organotin products of formula R 3 Sn-A. Nitriles and nitro-compounds, with α-hydrogen atoms, and acetone are believed to behave similarly in the prima...
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#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 35
#2Monique Biesemans (Vrije Universiteit Brussel)H-Index: 35
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An overview is given of the research performed by the authors at the Universite Libre de Bruxelles and Vrije Universiteit Brussel, including the kinetics, stereochemistry and mechanism of SE2 reactions at a saturated carbon atom, the synthesis of chiral organotin compounds and their configurational and optical stability, the fluxionality of trigonal bipyramidal metal atoms and the stereochemistry of SN2 reactions at tetrahedrally substituted P, Si, Ge, Sn atoms, the cytotoxicity of many series o...
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 35
Many organotin compounds are optically stable for long periods so that all the reactions transforming one of them into another can be studied from the stereochemical point of view. Several stereoselective reactions at tin have already been found. However the stereochemistries and even the stereoselectivities have not yet been determined (if the H—D exchange is not taken into account) because the optical purities (and a fortiori the absolute configurations) of the starting materials and of the re...
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
#2Ivan Vanden Eynde (Vrije Universiteit Brussel)H-Index: 6
The configurational stability of triorganostannyl–iron, –manganese and –cobalt complexes has been determined by studying the coalescence of the NMR signals of diastereotopic groups and by looking at the epimerization of diastereomeric mixtures of these compounds. Possible substitution reactions, transforming the studied derivatives into one another, have been checked.
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#2Kurt J. Irgolic (A&M: Texas A&M University)H-Index: 35
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
#2Yves Tondeur (ULB: Université libre de Bruxelles)H-Index: 6
Optically active triorganotin hydrides have been synthesized by asymmetric reduction of the corresponding halides. These optically stable compounds undergo stereoselective conversions into other optically stable compounds such as tetraorganotin compounds (by reaction with diazomethane or with bifluorenylidene) or hexaorganoditin compounds (by reaction in the presence of palladium) or into optically unstable compounds such as methylneophylphenyltin chloride (by reaction with CCl4). The HD exchan...
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#1Marcel GielenH-Index: 25
#2Yves Tondeur (ULB: Université libre de Bruxelles)H-Index: 6
Abstract The first optically-active triorganotin hydrides are reported viz.: (+)−and ()-methylneophylphenyltin hydride and ()-t-butylneophylphenyltin hydride; they are fairly optically stable.
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