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Organometallic compounds. Part IX: Synthesis of a series of racemic tetraorganotin compounds

Published on Sep 2, 2010in Recueil des Travaux Chimiques des Pays-Bas
· DOI :10.1002/recl.19680870912
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Jacques Nasielski15
Estimated H-index: 15
(ULB: Université libre de Bruxelles),
J. Topart7
Estimated H-index: 7
(ULB: Université libre de Bruxelles)
Abstract
  • References (4)
  • Citations (18)
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References4
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#1Stéphane Boué (ULB: Université libre de Bruxelles)H-Index: 8
#2Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 35
Last. Jacques Nasielski (ULB: Université libre de Bruxelles)H-Index: 10
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#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 35
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#1Marcel Gielen (ULB: Université libre de Bruxelles)H-Index: 25
#2G. Mayence (ULB: Université libre de Bruxelles)H-Index: 5
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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
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
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A redistribution of s-character in the tin orbitals of the Sn–C bonds of methyl-substituted tetraorganotins R3SnR' are expected to depend on the steric requirements of the R and R' groups and might be held responsible for the differences found for the J(Sn–C–H) coupling constants.
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#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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#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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#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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#1Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
#2Mohamed Acheddad (ULB: Université libre de Bruxelles)H-Index: 3
Last. Rudolph Willem (Vrije Universiteit Brussel)H-Index: 38
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The 1H NMR spectra in the pyridine proton region of six 2,6‐pyridinedicarboxylato‐(phenyl) (organo)tin(IV) compounds in DMSO‐d6 solutions exhibit a pattern that, together with 13C coupling data and 119Sn chemical shifts, can be interpreted by a heptacoordinated pentagonal bipyramidal structure in which the tin atom is likely to be surrounded by two DMSO ligands in equatorial positions. Copyright © 1991 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
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#1Bertha De Poorter (Vrije Universiteit Brussel)H-Index: 7
#2Marcel Gielen (Vrije Universiteit Brussel)H-Index: 25
The synthesis of a series of mixed and asymmetric benzyltin compounds is described. The nuclear magnetic resonance spectra are discussed.
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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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Diastereomeric ratio of optically active organotin compounds, R2*SnX2 and R1R2R3SnR*, was successfully determined by means of 119Sn NMR spectra.
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