- Stereoselective addition of cyanide reagents to nitrones
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An exploration of the diastereoselective addition of cyanide reagents to the nitrone 1 derived from D-glyceraldehyde acetonide to afford mixtures of syn-2 and anti-2 is presented. Trimethylsilyl cyanide was found to add to the nitrone 1 with essentially complete syn-stereoselectivity in excellent yields.
- Merchan, Francisco L.,Merino, Pedro,Tejero, Tomas
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- Cyclometalated Arylazo Compounds. Part 4. ortho-Cyano-1-aryazonaphthalenes and 3-Amino-2-arylbenzoindazoles from Cyclopalladated 1-Arylazonaphthalenes
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The reaction of a cyclopalladated 1-arylazonaphthalene with tetrabutylammonium cyanide leads to an orto-cyano-1-arylazonaphthalene and a 3-amino-aryl-benzoindazole, depending upon whether triphenylphosphine or 1,2-bis(diphenylphosphino)ethane (DIPHOS) is used to monomerize the binuclear Pd(II)-complex.In a similar insertion reaction with cyclohexyl isocyanide the corresponding 3-(N-cyclohexyl)-aminoindazole is formed.A Pd(II)-isocyano complex is shown to be a possible intermediate in that conversion.
- Gehrig, Kurt,Klaus, Alfred J.,Rys, Paul
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- Syntheses and anion binding capabilities of bis(diarylboryl) ferrocenes and related systems
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Isomeric diborylated ferrocenes featuring 1,1′-, 1,2-, and 1,3-substitution patterns have been targeted via a combination of electrophilic aromatic substitution and directed ortho-lithiation protocols. While none of these systems are competent for the Lewis acid chelation of fluoride, related systems featuring a mixed B/Si acceptor set capture 1 equiv of fluoride via a Si-F-B bridging motif.
- Kelly, Michael J.,Broomsgrove, Alexander E.J.,Morgan, Ian R.,Siewert, Inke,Fitzpatrick, Philip,Smart, Jessica,Vidovic, Dragoslav,Aldridge, Simon
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p. 2674 - 2684
(2013/06/26)
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- IONIC COMPOUND, PROCESS FOR PRODUCING SAME, AND ION-CONDUCTIVE MATERIAL COMPRISING SAME
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The present invention provides a method of producing a tetracyanoborate-containing ionic compound in a milder condition more efficiently and less expensively than conventional methods, and a tetracyanoborate-containing ionic compound having a reduced content of impure components. An ionic compound of the present invention is represented by the following general formula (I), has a content of fluorine atom-containing impurities of 3 mol% or less per 100 mol% of the ionic compound, and a method for producing an ionic compound represented by the general formula (I) of the present invention comprises a step of reacting starting materials containing a cyanide and a boron compound. (In the formula, Ktm+ denotes an organic cation [Kt b]m+ or an inorganic cation [Kta]m+; and m denotes an integer of 1 to 3.)
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Page/Page column 39
(2011/06/23)
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- Synthesis of a C3-symmetric furyl-cyclopeptide platform with anion recognition properties
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A new furyl amino acid derivative was trimerized to give a linear peptide and finally was cyclized. The newly generated cyclopeptide was subjected to a conformational study in order to be considered as a C3-symmetric platform for the ratio nal design of complex receptors. Moreover, the recognition properties towards cyanide, acetate and chloride anions were studied.
- Molina, Lidia,Moreno-Clavijo, Elena,Moreno-Vargas, Antonio J.,Carmona, Ana T.,Robina, Inmaculada
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experimental part
p. 4049 - 4055
(2010/09/10)
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- Applications of Phase-Transfer Catalysis, 31. - Tandem-Nucleophile-Electrophile Additions to Alkenes under Phase-Transfer Catalysis
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One-pot Michael additions/alkylations of diethyl benzylidenemalonate and ethyl (1-methylpropylidene)cyanoacetate (3) with alkali metal cyanide/phase-transfer (PT) catalyst and alkyl halides in halohydrocarbon solvents yield compounds 2a-f and 4a-d, respectively.It is noteworthy that no conversions occur in the total absence of traces of water.Cinnamates and methacrylates can be cyclo-dimerized by the action of solid cyanide/PT catalyst to give compounds 6 or 8, respectively.
- Dehmlow, Eckehard V.,Kunesch, Ernst
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p. 1904 - 1909
(2007/10/02)
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- PHOSPHORORGANISCHE VERBINDUNGEN 90 Methodische Ausgestaltung der P-C und P-S-Cyanolyse am Beispiel einiger Heterophosphoniumsalze
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Treatment of allylamido-phosphonium salts with dry tetrabutylammonium cyanide in methylenechloride delivers after removal of the allyl group phosphinous acid amides with retention of configuration (P-C-cyanolysis).Allyl-O-alkylphosphonium salts undergo the Arbosov reaction under the above conditions, while allyl-S-alkyl phosphonium salts undergo fission of the P-S bond (P-S cyanolysis).Equally good results were obtained using KCN in methylene chloride accompained by catalytic amounts of 18-crown-6 ether; thus optically active benzyl-methyl-phenyl-phosphine-sulfid gave the corresponding phosphine with retention of configuration.Dithiophosphinic acid esters and thiophosphinic acid amides, after conversion to the corresponding quasiphosphonium salts via S-alkylation and subsequent treatment with tetrabutylammonium cyanide in methylenechloride, also give the corresponding thiophosphinous acid ester and phosphinous acid amide respectively.Thiophosphinic acid O-alkyl esters (R2P(S)OR') give however the thiophosphinic S-alkyl ester (R2P(O)SR') via an Arbusov reaction.The P-C cyanolysis of allyl-triphenylphosphoniumbromide using KCN/18-crown-6 or tetrabutylammonium cyanide in aprotic medium stops at the stage of the intermediary red-coloured ylide; addition of a proton-donor then results in the subsequent rearrangement to the corresponding propenyl-phosphonium salt.
- Horner, Leopold,Jordan, Manfred
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p. 215 - 220
(2007/10/02)
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