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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)
Cite
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 (18)
  • Citations (25)
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References18
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
Stéphane Boué7
Estimated H-index: 7
(ULB: Université libre de Bruxelles),
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles)
+ 2 AuthorsRichard Spielmann2
Estimated H-index: 2
(ULB: Université libre de Bruxelles)
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
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)
Marcel Gielen25
Estimated H-index: 25
(ULB: Université libre de Bruxelles),
Jacques Nasielski17
Estimated H-index: 17
(ULB: Université libre de Bruxelles),
J. Topart7
Estimated H-index: 7
(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 4, 2007in Journal of Chemical Technology & Biotechnology
G. J. M. Der Van Kerk7
Estimated H-index: 7
,
J. G. Noltes3
Estimated H-index: 3
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.
Published on Nov 1, 1974in Annals of the New York Academy of Sciences4.29
Marcel Gielen34
Estimated H-index: 34
(ULB: Université libre de Bruxelles),
Hassan M. Jamaï1
Estimated H-index: 1
(ULB: Université libre de Bruxelles)
Published on May 1, 1972in Journal of the American Chemical Society14.70
C. E. Holloway1
Estimated H-index: 1
,
S. A. Kandil1
Estimated H-index: 1
,
I. M. Walker1
Estimated H-index: 1
Published on Mar 1, 1970in Journal of Organometallic Chemistry2.07
Kenneth C. Williams4
Estimated H-index: 4
(Ethyl Corporation)
Abstract The preparation, properties, and reactions of trimethylplumbylmagnesium chloride and triethylplumbylmagnesium chloride are described. The complexes are highly reactive and fairly stable intermediates in the reaction of Grignard reagents with lead(II) salts in the presence of alkyl halides to give tetraalkyllead compounds. Some new organolead and silicon-substituted organolead compounds are reported.
Cited By25
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),
Hassan Mokhtar-Jamaï4
Estimated H-index: 4
(ULB: Université libre de Bruxelles)
The optical stability of methylneophyltrityltin halides is greater than that of less sterically hindered triorganotin halides.
Published on Sep 1, 2010in Bulletin des Sociétés Chimiques Belges
Marcel Gielen25
Estimated H-index: 25
(Vrije Universiteit Brussel),
Yves Tondeur6
Estimated H-index: 6
(ULB: Université libre de Bruxelles)
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
Published on Dec 15, 2009in Patai's Chemistry of Functional Groups
James A. Marshall23
Estimated H-index: 23
(USC: University of South Carolina),
Jill 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
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
M. Belén Faraoni3
Estimated H-index: 3
(UNS: Universidad Nacional del Sur),
Alicia D. Ayala7
Estimated H-index: 7
(UNS: Universidad Nacional del Sur)
+ 3 AuthorsJulio C. Podestá13
Estimated H-index: 13
(UNS: Universidad Nacional del Sur)
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 ...
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 May 1, 2004in Journal of Organometallic Chemistry2.07
Michael Veith23
Estimated H-index: 23
(Saarland University),
Andreas Rammo9
Estimated H-index: 9
(UPMC: Pierre-and-Marie-Curie University)
+ 2 AuthorsDominique Agustin2
Estimated H-index: 2
(UPMC: Pierre-and-Marie-Curie University)
Abstract Reaction of tin tetrachloride with the appropriate Grignard reagent gave Sn[C 6 H 4 –CH(OCH 2 ) 2 ] 4 ( 2 ), which was transformed to Sn[C 6 H 4 –CHO] 4 ( 3 ) and its hydrazido and amino derivatives Sn[C 6 H 4 –CHN–NH–C 6 H 3 -2,4-(NO 2 ) 2 ] 4 ( 5 ) and Sn{C 6 H 4 –CH[N(C 2 H 4 ) 2 O] 2 } 4 ( 8 ). Oxidation of ( 3 ) produced Sn[C 6 H 4 –COOH] 4 ( 4 ) while reduction of ( 3 ) gave Sn[C 6 H 4 –CH 2 –OH] 4 ( 6 ). From the acid 4 , an amino acid Sn[C 6 H 4 –CO–NH–CH 2 –CO–OCH 3 ] 4 ( 7 ) ...
View next paperConfigurational Stability of Triorganostannylamines, ‐Phosphines and ‐Arsines