595-90-4Relevant articles and documents
Studies of organotin(IV)-orthoquinone systems
Brown, Martyn A.,McGarvey, Bruce R.,Ozarowski, Andrzej,Tuck, Dennis G.
, p. 165 - 172 (1998)
The primary process in the reaction of hexaphenylditin with various substituted orthoquinones (Q) is shown to involve attack by the quinone at a phenyl ligand. The intermediate thus formed decomposes to yield Ph3Sn(SQ·), where S(Q·-) is the corresponding semiquinonate. Rearrangement of these species in solution gives rise to biradicals, while intramolecular electron transfer may lead to the formation and precipitation of Ph2Sn(CAT), where CAT2- is the corresponding substituted catecholate. The identification of these processes depends in part on electron paramagnetic resonance spectroscopy. The reaction of Ph3SnCl or Ph2SnCl2 with Na(TBSQ·) (TBSQ·- = 3,5-di-tert-butyl-orthobenzosemiquinonate) results in the formation of Ph2Sn(TBSQ·), which can undergo redistribution and intramolecular electron transfer, so that the solution chemistry of these latter systems is similar to that of the products of the Sn2Ph6 + Q reaction.
Calcium stannyl formation by organostannane dehydrogenation
Morris, Louis J.,Hill, Michael S.,Manners, Ian,Mcmullin, Claire L.,Mahon, Mary F.,Rajabi, Nasir A.
, p. 12964 - 12967 (2019)
Reaction of the dimeric calcium hydride, [(BDI)CaH]2 (1), with Ph3SnH ensues with elimination of H2 to provide [(BDI)Ca-μ2-H-(SnPh3)Ca(BDI)] (3) and [(BDI)Ca(SnPh3)]2 (4) alongside dismutation to Ph4Sn, H2 and Sn(0). DFT analysis indicates that stannyl anion formation occurs through deprotonation of Ph3SnH and with retention of dinuclear species throughout the reactions.
The photochemistry of aromatic compounds IV. Photochemical behaviour of hexaphenylditin
Wilputte-Steinert,Nasielski
, p. 113 - 118 (1970)
The irradiation of hexaphenylditin yields "hot" triphenyltin radicals whose decomposition into diphenyltin and phenyl radicals competes with recombination and disproportionation.
The reactions of Ir(CO)Cl(PPh3)2 with HSnPh 3
Adams, Richard D.,Fang, Fang,Smith, Mark D.,Zhang, Qiang
, p. 2904 - 2909 (2011)
A reinvestigation of the reaction of Ir(CO)Cl(PPh3)2, 1 with HSnPh3 has revealed that the oxidative-addition product Ir(CO)Cl(PPh3)2(H)(SnPh3), 2 has the H and SnPh3 ligands in cis-related coordination sites. Compound 2 reacts with a second equivalent of HSnPh3 by a Cl for H ligand exchange to yield the new compound H2Ir(CO)(SnPh3)(PPh 3)2, 3. Compound 3 contains two cis- related hydride ligands. Under an atmosphere of CO, 1 reacts with HSnPh3 to replace the Cl ligand with SnPh3 and one of the PPh3 ligands with a CO ligand and also adds a second equivalent of CO to yield the 5-coordinate complex Ir(CO)3(SnPh3)(PPh3), 4. Compound 4 reacts with HSnPh3 by loss of CO and oxidative addition of the Sn-H bond to yield the 6-coordinate complex HIr(CO)2(SnPh 3)2(PPh3), 5 that contains two trans-positioned SnPh3 ligands.
The structures of ring-expanded NHC supported copper(
Charman, Rex S. C.,Liptrot, David J.,Lowe, John P.,Mahon, Mary F.
supporting information, p. 831 - 835 (2022/02/01)
Three ring-expanded N-heterocyclic carbene-supported copper(i) triphenylstannyls have been synthesised by the reaction of (RE-NHC)CuOtBu with triphenylstannane (RE-NHC = 6-Mes, 6-Dipp, 7-Dipp). The compounds were characterised by NMR spectroscopy and X-ray crystallography. Reaction of (6-Mes)CuSnPh3 with di-p-tolyl carbodiimide, phenyl isocyanate and phenylisothiocyanate gives access to a copper(i) benzamidinate, benzamide and benzothiamide respectively via phenyl transfer from the triphenylstannyl anion with concomitant formation of (Ph2Sn)n. Attempts to exploit this reactivity under a catalytic regime were hindered by rapid copper(i)-catalysed dismutation of Ph3SnH to Ph4Sn, various perphenylated tin oligomers, H2 and a metallic material thought to be Sn(0). Mechanistic insight was provided by reaction monitoring via NMR spectroscopy and mass spectrometry.
Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes
Liu, Yuxia,Wang, Chao,Huang, Linjuan,Xue, Dong
, p. 1613 - 1618 (2020/09/15)
A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.
Continuous organomagnesium synthesis of organometallic compounds
Storozhenko,Grachev,Klochkov,Shiryaev
, p. 387 - 393 (2013/06/27)
Continuous organomagnesium synthesis of a number of organic derivatives of 14th group elements of the periodic table was examined in a column apparatus with an agitator. An effect of a molar ratio of reactants, temperature in a reaction zone, and other factors was studied on the yield and composition of the products.
Quest for triorganotin(IV) compounds containing three C,N- and N,C,N-chelating ligands
R??i?ka, Ale?,Padělková, Zdeňka,?vec, Petr,Pejchal, Vladimír,?eslová, Lenka,Hole?ek, Jaroslav
, p. 47 - 57 (2013/06/27)
Three novel tetraorganotin(IV) compounds of general formula L 3SnR [where i) L is LCN 2-(N,N-dimethylaminomethyl)phenyl- and R = n-Bu (1), Ph (2); and ii) L is LNCN 2,6-bis-(N,N- dimethylaminomethyl)phenyl- with R = n-Bu (3)] were synthesized. These species were used as potential precursors for the target preparation of some triorganotin(IV) species of general formula L3SnX [where i) L is LNCN with X = OH (4), and ii) L is LCN and X = Br (5), F (5b), Cl (5c)]. Several methods were applied to reach the target L 3SnX molecules including the reactions of 1 or 2 with bromine, iodine or hydrohalic acids in various media, Kocheshkov reactions or transmetallation with HgCl2, but the composition of all reaction mixtures was not satisfactory towards the target. Compound 4 has the monomeric structure with OH group interacting with one of the nitrogen atoms via H-bridge. Target compound 5 was prepared by the reaction of three equivalents L4CNSn with SnBr4 followed by the isolation of 5 from the reaction mixture based on different solubility of 5 in various solvents. Surprisingly, the presumably air-stable 5 can easily ionize in the air to give a novel aqua-complex [L3CNSn(H 2O)]+Br- (5a). All prepared organotin(IV) compounds bearing both LCN and LNCN ligands were characterized by multinuclear NMR spectroscopy and, when eligible, by the elemental analysis. In addition, the solid-state structures of 1, 2, 4, 5a, 6, 8 and 9 were determined by the X-ray diffraction analysis.
A convenient route to distannanes, oligostannanes, and polystannanes
Khan, Aman,Gossage, Robert A.,Foucher, Daniel A.
, p. 1046 - 1052 (2011/02/16)
The quantitative conversion of the tertiary stannane (ν;-Bu) 3SnH (2) into (ν-Bu)6Sn2 (4) was achieved by heating the neat hydride material under low pressure or under closed inert atmosphere conditions. A 31% conversion of Ph3SnH (3)to Ph6Sn 2 (5) was also observed under low pressure; however, under closed inert atmosphere conditions afforded Ph4Sn (6) as the major product. A mixed distannane, (ν-Bu)3SnSnPh3 (7), can also be prepared in good yield utilizing an equal molar ratio of 2 and 3 and the same reaction conditions used to prepare 4. This solvent-free, catalyst-free route to distannanes was extended to a secondary stannane, (ν-Bu)2SnH 2 (8), which yielded evidence (NMR) for hydride terminated distannane H(ν-Bu)2SnSn(ν-Bu)2H(9), the polystannane [(ν-Bu)2Sn] ' (10), and various cyclic stannanes [(ν- Bu)2Sn]ν=5,6=5,6 (11, 12). Further evidence for 10 was afforded by gel permeation chromatography (GPC) where a broad, moderate molecular weight, but highly dispersed polymer, was obtained (Mw = 1.8 × 104 Da, polydispersity index (PDI) = 6.9) and a characteristic UV-vis absorbance (1max)of ν370 nm observed.
The Ullmann coupling reaction: A new approach to tetraarylstannanes
Shaikh, Nadim S.,Parkin, Sean,Lehmler, Hans-Joachim
, p. 4207 - 4214 (2008/10/09)
Several iodobenzenes form tetraarylstannanes, in addition to other products, under reaction conditions typically employed for the Ullmann reaction, i.e., activated copper bronze (a copper-tin alloy) and 7 days at 230°C. The isolated yields of the tetraarylstannanes were low to good (8-58%). Significantly higher yields (54-64%) of tetraphenylstannane were obtained by the direct reaction of iodobenzene with an excess of tin powder (iodobenzene: tin = 1:1 w/w) under the same conditions. Crystal structure analysis reveals that tetrakis(4-carbomethoxyphenyl)stannane crystallizes in a tetragonal space group and has 4 symmetry, which is the case for many symmetrical tetraarylstannanes. However, tetrakis(2,4-dichlorophenyl)stannane, tetrakis(3,4-dichlorophenyl)stannane, and tetrakis(2,4-dimethylphenyl)stannane do not crystallize in a tetragonal space group and do not have real 4 symmetry.
