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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)
Cite
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
  • References (10)
  • Citations (11)
Cite
References10
Newest
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Stéphane Simon1
Estimated H-index: 1
(Vrije Universiteit Brussel)
+ 2 AuthorsCornelis Hoogzand9
Estimated H-index: 9
(Vrije Universiteit Brussel)
Methylneophylphenyltin hydride (I), (methylneophylphenylstannyl) cyclopentadienyl molybdenum tricarbonyl(II) and dimethylphenylstannylmethyl-α-naphthyl-phenylgermanium (III) are configurationally stable within the NMR time scale, even in the presence of strong nucleophiles.
Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Hassan Mokhtar-Jamaï4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
The synthesis of optically active p‐anisyl‐(3‐hydroxy‐3‐methylbutyl)methyl‐α‐naphthyl tin (IV) is described. The spectroscopic properties of this compound and of the products used as synthesis intermediates are given. The two diastereoisomers of (‐)‐menthyl‐β‐(methylnaphthyl‐phenylstannyl)‐propionate (V) could not be separated. Copyright © 1975 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
M. De Clercq4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
+ 3 AuthorsH. Vanwuytswinkel1
Estimated H-index: 1
(ULB: Université libre de Bruxelles)
Published on May 4, 2007in Journal of Chemical Technology & Biotechnology
G.J.M. van der Kerk25
Estimated H-index: 25
,
J. G. Noltes12
Estimated H-index: 12
,
J. G. A. Luijten13
Estimated H-index: 13
The preparation, according to the slightly modified procedure of Finholt et al., of the following organo-tin hydrides is described: triethyltin hydride, tri-n-propyltin hydride, tri-n-butyltin hydride, triphenyltin hydride, di-n-propyltin dihydride, di-n-butyltin dihydride, diphenyltin dihydride and n-butyltin trihydride. In addition, the preparation of the intermediate n-butyltin trichloride is described.
Published on May 27, 1975in Journal of Organometallic Chemistry2.07
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Hassan Mokhtar-Jamaï4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
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.
Published on Jan 16, 1972in Journal of Organometallic Chemistry2.07
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
M. De Clercq4
Estimated H-index: 4
(ULB: Université libre de Bruxelles),
Bertha De Poorter7
Estimated H-index: 7
(Vrije Universiteit Brussel)
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.
Published on Dec 1, 1969in Angewandte Chemie12.26
H. Schumann1
Estimated H-index: 1
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.
Published on Apr 1, 1965in Journal of Organometallic Chemistry2.07
K. Jones1
Estimated H-index: 1
(University of Manchester),
M.F. Lappert5
Estimated H-index: 5
(University of Manchester)
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...
Published on Feb 1, 1962in Journal of Organic Chemistry4.75
Christ Tamborski22
Estimated H-index: 22
,
Frederic E. Ford3
Estimated H-index: 3
+ 2 AuthorsEdward J. Soloski9
Estimated H-index: 9
Cited By11
Newest
Published on Jan 1, 2012
Jean-Paul Quintard21
Estimated H-index: 21
(University of Nantes),
E. Le Grognec19
Estimated H-index: 19
(University of Nantes)
The synthesis of chiral molecules or complexes containing tin(IV) and tin(II) is reported considering the type of chirality and the nature of the bonding to tin. The tin-centered chirality is first examined considering different types of functionalization and focusing on the configurational stability at the tin center, which provides useful information for organometallic chemists. Chiral ligands C -linked, O -linked, or N -linked to tin have been subsequently considered focusing first on the syn...
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
S. Simon7
Estimated H-index: 7
(ULB: Université libre de Bruxelles)
(Dimethylphenylstannyl)methyl‐1‐naphthyl‐phenylgermanium (I) and methylneophylphenyl (triphenylgermyl)tin (II) are configurationally stable even in the presence of strong nucleophiles. Optically active isopropylmethylphenyl (triphenylgermyl)tin (III) has been synthesized by asymmetric induction and shows that hexaorganodimetal compounds with a tin‐germanium bond are optically stable. The synthesis of functionally substituted organometallic compounds with a Sn‐Ge bond, like 5‐[(phenyldimethylstan...
Published on Feb 26, 2007
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles)
Published on Apr 1, 2005in Applied Organometallic Chemistry3.26
Marcel Gielen34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Monique Biesemans34
Estimated H-index: 34
(Vrije Universiteit Brussel),
Rudolph Willem38
Estimated H-index: 38
(Vrije Universiteit Brussel)
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...
Published on Jan 1, 1980in Israel Journal of Chemistry2.22
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Ivan Vanden Eynde7
Estimated H-index: 7
(Vrije Universiteit Brussel)
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.
Published on Apr 17, 1979in Journal of Organometallic Chemistry2.07
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Yves Tondeur6
Estimated H-index: 6
(ULB: Université libre de Bruxelles)
Abstract 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 CCl 4 ). The...
Published on Jan 1, 1976in Israel Journal of Chemistry2.22
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Serge Simon1
Estimated H-index: 1
(ULB: Université libre de Bruxelles)
+ 3 AuthorsIvan Vanden Eynde7
Estimated H-index: 7
(Vrije Universiteit Brussel)
Several classes of organotin compounds are configurationally stable within the NMR time-scale and are even optically stable for weeks. Optically active tetraorganotin compounds, triorganotin hydrides and an optically active (triorganogermyl)triorganotin compound have been synthesized. Two reactions transforming optically active triorganotin hydrides into optically active tetraorganotin compounds are described.
View next paperThree new classes of configurationally stable organotin compounds