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Synthesis of the First Optically Active Tetraorganotin Compound in Which the Tin Atom Is The Only Chiral Center

Published on Sep 2, 2010in Bulletin des Sociétés Chimiques Belges
· DOI :10.1002/bscb.19750840310
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Hassan Mokhtar-Jamaï4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
Abstract
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
  • References (19)
  • Citations (25)
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References19
Newest
#1Stéphane Boué (ULB: Université libre de Bruxelles)H-Index: 8
#2Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
Last. Richard Spielmann (ULB: Université libre de Bruxelles)H-Index: 2
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Nine new racemic organotin derivatives: MePriPrSnR (R = Br, Et, Bu, iBu, sBu, tBu) and MeiPrcycloHexSnR′ (R′ = Br, Et, anisyl) have been synthesized in high yields. Their mass spectra and those of some intermediates are given and discussed on the basis of previous results. Copyright © 1969 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
23 CitationsSource
#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
#2Jacques Nasielski (ULB: Université libre de Bruxelles)H-Index: 15
Last. J. Topart (ULB: Université libre de Bruxelles)H-Index: 7
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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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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.
12 CitationsSource
#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
#2M. De Clercq (ULB: Université libre de Bruxelles)H-Index: 4
Last. H. Vanwuytswinkel (ULB: Université libre de Bruxelles)H-Index: 1
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9 CitationsSource
#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
#2Bertha De Poorter (Vrije Universiteit Brussel)H-Index: 7
Last. J. Topart (ULB: Université libre de Bruxelles)H-Index: 7
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The synthesis of racemic tetraalkyltin compounds is described, starting from tributyltin chloride and using alternating Grignard syntheses and bromodemetallations in alcohols. The mass spectra of the obtained tetra‐ and triorganotin derivatives are given as analytical evidence for their obtainment. Copyright © 1973 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
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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.
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Reactions of cyanoalkyl- and methoxycarbonylalkyl-tin compounds with lithium aluminium hydride and Grignard reagents have been studied. Several new organo-tin compounds containing hydroxyalkyl, aminoalkyl and ketoalkyl groups are described.
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#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 35
#2Hassan M. Jamaï (ULB: Université libre de Bruxelles)H-Index: 1
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Cited By25
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#1Jean-Paul Quintard (University of Nantes)H-Index: 22
#2E. Le Grognec (University of Nantes)H-Index: 19
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...
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
#2Yves Tondeur (ULB: Université libre de Bruxelles)H-Index: 6
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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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 35
#2Hassan Mokhtar-Jamaï (ULB: Université libre de Bruxelles)H-Index: 4
The optical stability of methylneophyltrityltin halides is greater than that of less sterically hindered triorganotin halides.
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 35
#2Stéphane Simon (ULB: Université libre de Bruxelles)H-Index: 7
Racemic p-(cyclohexylmethyl-l-naphthylstannyl) acetophenone (I) is transformed into its menthydrazone which is, after four recrystallizations, reconverted to optically active (I), [α]20°436 +0.25° ± 0.05°. Several methods have been used to determine the optical purity of optically active (I) without success.
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#1James A. Marshall (USC: University of South Carolina)H-Index: 16
#2Jill A. Jablonowski (USC: University of South Carolina)
1 Introduction 2 Chiral Organometallics of Type R1R2R3R4M 3 Germacyclopentanes and Cyclohexanes 4 Organometallics of Type R*MR3 5 Propargyl/Allenyl Systems Keywords: chiral organometallics of Type R1R2R3R4M; tin and configurational stability; pentacoordinated triorgano halostannanes; germacyclopentanes and cyclohexanes; organometallics of type R*MR3; chiral acyclic systems; propargyl/allenyl systems; germacyclopentanes and cyclohexanes
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#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
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#1M. Belén Faraoni (UNS: Universidad Nacional del Sur)H-Index: 3
#2A. D. Ayala (UNS: Universidad Nacional del Sur)H-Index: 7
Last. Julio C. Podestá (UNS: Universidad Nacional del Sur)H-Index: 13
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A key step in the preparation of asymmetric heterogeneous catalysts based on silica-supported rhodium and platinum chemically modified with chiral organotins, is the synthesis of optically pure tin derivatives. We report on the synthetic pathways leading to the synthesis of (−)-menthyltin derivatives without the formation of epimerization by-products. The physical properties (including full 1H, 13C and 119Sn NMR spectra) of the new compounds, containing between one and three (−)-menthyl ligands ...
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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 35
#2Monique Biesemans (Vrije Universiteit Brussel)H-Index: 35
Last. Rudolph Willem (Vrije Universiteit Brussel)H-Index: 38
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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...
160 CitationsSource