Tin Hydride

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Dennis P Curran - One of the best experts on this subject based on the ideXlab platform.

  • synthesis of tris 2 perfluorohexylethyl Tin Hydride a highly fluorinated Tin Hydride with advantageous features of easy purification
    Organic Syntheses, 2003
    Co-Authors: Aimee Crombie, Sunyoung Kim, Sabine Hadida, Dennis P Curran
    Abstract:

    Tris (2-perfluorohexylethyl-Tin Hydride R PhenylTin trichloride I Tris (2-perfluorohexylethyl)phenylTin 1 Bromotris [2-(perfluorohexyl)ethyl]Tin 2 P Tris (2-perfluorohexylethyl-Tin Hydride Keywords: organometallic compounds, magnesium; metalation reactions, magnesium; halogen compounds, fluorine compounds; halogen compounds, iodine compounds; halogen compounds, fluorine compounds; metalation reactions, Tin; organometallic compounds, Tin; organometallic compounds, Tin; halogenation, bromination; halogen compounds, bromine compounds; replacement reactions, miscellaneous; reduction, CX  CH; organometallic compounds, Tin; replacement reactions, halogen by hydrogen; replacement reactions, miscellaneous; halogen compounds, fluorine compounds; metalation reactions, Tin

  • tris 2 perfluorohexylethyl Tin Hydride
    e-EROS Encyclopedia of Reagents for Organic Synthesis, 2003
    Co-Authors: Zhiyong Luo, Dennis P Curran
    Abstract:

    [175354-32-2] C24H13F39Sn (MW 1161.01) InChI = 1S/3C8H4F13.Sn.H/c3*1-2-3(9,10)4(11,12)5(13,14)6(15,16)7(17,18)8(19,20)21;;/h3*1-2H2;; InChIKey = XDEOXVCAUPQFMU-UHFFFAOYSA-N (a substitute for tributylTin Hydride in radical reactions with easy work up procedure to remove Tin residues;1 reduction of halides, nitro compounds, phenylselenides, and xanthates;2 promotes radical cyclizations and Giese reactions; hydrostannation of alkenes and alkynes; hydroxymethylation of halides under high pressure of CO;3 a useful reagent for reactions carried out in supercritical CO2).4 Alternate Name: Tris-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooc-tyl)stannane; Curran–Hadida reagent. Physical Data: bp 115 °C/0.1 mmHg. Solubility: insoluble or sparingly in most organic solvents such as chloroform, dichloromethane, benzene, tert-butanol, and tolu-ene; soluble in perfluorocarbon solvents, for example, perfluoromethylcyclohexane (PFMC) and FC-72 (mixture of isomers of perfluorohexane); partially fluorinated solvents, for example, benzotrifluoride (BTF); ethereal solvents, for example, diethyl ether and supercritical CO2 (scCO2). Form Supplied in: clear, colorless, odorless liquid; will be commercialized by Fluorous technologies, Inc. (www.fluorous.com). Preparative Methods: generation of a Grignard reagent from perfluorohexylethyl iodide and quenching with trichlorophenylTin gave a fluorous phenyl Tin compound. Bromolysis of the Sn–Ph bond followed by reduction with LAH gave tris(2-perfluoroh-exylethyl)Tin Hydride in 65% overall yield (eq 1).2, 5 (1) Handling, Storage, and Precautions: the toxicity of the fluorous Tin Hydride has not been examined. However, alkylTin compounds are generally toxic and should be handled with care in a fume hood. The reagent should be stored in a refrigerator under nitrogen atmosphere and kept away from light and air.

  • The Tin Hydride Reductive Decyanation of Geminal Dinitriles
    Synlett, 2002
    Co-Authors: Dennis P Curran, C. M. Seong
    Abstract:

    Mono- and dialkylated malononitriles (geminal dinitriles) are reductively decyanated to mononitriles (10 examples) on treatment with tributylTin Hydride and a catalytic amount of 2,2′-azobisisobutyronitrile in refluxing benzene. A mechanism for this reaction is also proposed.

  • hydroxymethylation of organic halides evaluation of a catalytic system involving a fluorous Tin Hydride reagent for radical carbonylation
    Tetrahedron Letters, 1997
    Co-Authors: Ilhyong Ryu, Satoshi Minakata, Mitsuo Komatsu, Sabine Hadida, Tatsuro Niguma, Dennis P Curran
    Abstract:

    Abstract Hydroxymethylation of organic halides 2 using a catalytic amount of fluorous Tin Hydride 1 , CO, and NaBH 3 CN as a reducing agent, proceeded smoothly to give one-carbon homologated alcohols 5 in good yields. Three phase workup (water-dichloromethane-perfluorohexane) was conveniently performed for the separation of 1 and 5 .

  • rate constants for reaction of a fluorous Tin Hydride reagent with primary alkyl radicals
    Tetrahedron Letters, 1997
    Co-Authors: Dennis P Curran, John H Horner, Felix N Martinez, Martin Newcomb
    Abstract:

    Abstract Rate constants for 6-exo cyclization of the 7,7-diphenyl-6-heptenyl radical (3) in benzotrifluoride (BTF, PhCF3) were determined by laser flash photolysis, and radical clock 3 was used in competition kinetic studies for determination of rate constants of reactions of the fluorous Tin Hydride reagent tris(2-(perfluorohexyl)ethyl)Tin Hydride with primary alkyl radicals.

Ronald Breslow - One of the best experts on this subject based on the ideXlab platform.

James Light - One of the best experts on this subject based on the ideXlab platform.

Mitsuo Komatsu - One of the best experts on this subject based on the ideXlab platform.

Berthold Hoge - One of the best experts on this subject based on the ideXlab platform.

  • tris pentafluoroethyl stannane Tin Hydride chemistry with an electron deficient stannane
    Chemistry: A European Journal, 2018
    Co-Authors: Markus Wiesemann, Mark Niemann, Johannes Klosener, Beate Neumann, Hans-georg Stammler, Berthold Hoge
    Abstract:

    A versatile two-step synthesis of tris(pentafluoroethyl)stannane, HSn(C2F5)(3), is presented. Electron-withdrawing C2F5 groups significantly influence the polarity of the Tin-hydrogen bond, which allows facile deprotonation of the compound, even in water. The utility of this electron-deficient stannane was illustrated in hydrostannylations of alkenes and alkynes, as well as in dehalogenation reactions. The remarkably high reactivity of HSn(C2F5)(3) is demonstrated in fast hydrostannylations, even in the absence of activators, whereby the regioselectivity of this process turns out to be solvent dependent. It is of great advantage that in dehalogenation reactions volatile halogenotris(pentafluoroethyl)stannanes, XSn(C2F5)(3) (X=I, Br), are formed that allow facile separation of the Tin-containing byproducts from the reaction mixtures.

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