60385-55-9Relevant academic research and scientific papers
DIRECTED CLEAVAGE OF CARBON-TIN BONDS BY PALLADIUM
Suggs, J. William,Lee, Ken. S.
, p. 297 - 310 (1986)
The ligands 8-(trimethylstannyl)methylquinoline, n-Bu3Sn(CH2)3NMe2 and Ph3Sn(CH2)3NMe2 Ph3Sn(CH2)3NMe2 react with (C6H5CN)2PdCl2 to give five-membered palladium chelates, in which the nitrogen atom was able to direct palladium insertion into a specific carbon-tin bond.The X-ray crystal structure of the simple chelate 2 is presented.
Nucleophilic attack within Ge, Sn and Pb complexes containing Me2N(CH2)3 - As a potential intramolecular donor ligand
Zickgraf, Andrea,Beuter, Mike,Kolb, Ute,Dra?ger, Martin,Tozer, Ramon,Dakternieks, Dainis,Jurkschat, Klaus
, p. 203 - 214 (2008/10/08)
Thirteen tin compounds LxPhySnClz and LPh2SnPhX (x=1-4, y=0-3, z=0-2; X=Ph, F, Cl, Br, I, OPh), six germanium compounds LxPhyGeClz and four lead compounds LPh2PbPhX (X=Ph, Cl, Br, I) containing the potential intramolecular donor L = Me2N(CH2)3- have been synthesized by Grignard reactions, redistribution, halogenation, exchange of halide and phenylation. Evidence for 1,5-chelation in which the donor Me2N intramolecularly attacks the Lewis-acidic atoms Ge, Sn or Pb is provided by six crystal structure determinations: Me2N(CH2)3SnPh2Cl,5;Me 2N(CH2)3SnPh2Br,5a;Me 2N(CH2)3SnPh2I,5b;Me 2N(CH2)3SnPh2OPh,5d;Me 2N(CH2)3SnPh3·HCl·H2O, 1a; Me2N(CH2)3PbPh2I, 17b), and by solution 13C, 119Sn and 207Pb NMR data. This nucleophilic attack originates from the π-basicity and the charge flow from the ligands into a σ*-LUMO at Ge, Sn or Pb. The electronegativity of the ligands at Ge, Sn or Pb inhibits nucleophilic attack. The ligand sequences PhCl2>Ph2Cl>PhCl>Ph3 and Ph2I>Ph2Br>Ph2OPh>Ph 2Cl>Ph2F hold for an increasing approach (N?Ge/Sn/Pb). The δ values (13C) of the α-methylene in CDCl3 solution are shifted distinctly to high frequency by increasing the approach between the Me2N donor and the central atom. A qualitative discussion of 119Sn NMR chemical shifts and spin-spin coupling constants is given, which supports the arguments on the basis of interactions of frontier orbitals.
Utilization of hypervalently activated organotin compounds in synthesis. Preparation and reactions of Me2N(CH2)3SnPh3
Dakternieks, Dainis,Dyson, Gail,Jurkschat, Klaus,Tozer, Ramon,Tiekink, Edward R.T.
, p. 29 - 38 (2007/10/02)
The reaction of Me2N(CH2)3SnPh3 (1) with phenol gives Me2N(CH2)3Sn(OPh)nPh(3-n) (2, n = 1; 3, n = 2) in good yields.All the phenyl groups are cleaved off when 1 is treated with glycol or pinacol, resulting in the formation of 2(OC2H4O)3 (4) and 2(OC2Me4O)3 (5), respectively.Compounds 4 and 5 are transformed almost quantitatively into Me2N(CH2)3Sn(SPh)3 (6) and H (7) by reaction with phenyl mercaptan and trimethylchlorosilane, respectively.The reaction of 2 with triethanolamine and nitrilotriacetic acid affords the newstannatrane Me2N(CH2)3Sn(OCH2CH2)3N (8) and Me2N(CH2)3Sn(OCOCH2)3N (9), respectively.However, the N-oxide derivative Me2(O)N(CH2)3Sn(OCOCH2)3N (10) is obtained by reaction of 1 with N(CH2COOH)3 in DMF.Compounds 1-10 have been characterized by means of 1H, 13C and 119Sn NMR spectroscopy and mass spectrometry.The crystal structures of Me2N(CH2)3Sn(SPh)3 (6) and Me2(O)N(CH2)3Sn(OCOCH2)3N (10) have been determined by an X-ray diffraction study.The tin atom in 6 is trigonal bipyramidal with an intramolecular Sn-N distance of 2.605(6) Angstroem.Compound 10 contains an octahedral tin with intramolecular Sn-N and Sn-ON distances of 2.231(7) and 2.101(7) Angstroem, respectively.
