27610-88-4Relevant articles and documents
Dichloro(2,2,2-trifluoroethoxy)oxovanadium(V). A remarkably effective reagent for promoting one-electron oxidative cyclization and unsymmetrical coupling of silyl enol ethers [5]
Ryter,Livinghouse
, p. 2658 - 2659 (2007/10/03)
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NEW SYNTHESIS OF γ-DIKETONES
Gendin, D. V.,Petrov, P. A.,Mokov, A. S.,Voronkov, M. G.
, p. 1724 - 1727 (2007/10/02)
A new method of synthesizing γ-diketones by the reactions of bis(triethylsilyl)- or bis(triethylgermyl)-mercury with α-bromo ketones was developed.The reaction proceeds by a radical mechanism with the intermediate formation of silyl or germyl enol ethers.
Direct and Regiocontrolled Synthesis of α-Phenyl Ketones from Silyl Enol Ethers and Diphenyliodonium Fluoride
Chen, Kuanchiang,Koser, Gerald F.
, p. 5764 - 5767 (2007/10/02)
The efficiacy of diphenyliodonium fluoride (1, DIF) for the phenylation of silyl enol ethers was investigated.When the silyl enol ethers of cyclopentanone, 2-methylcyclopentanone, cyclohexanone, 2-methylcyclohexanone, acetophenone, 2-pentanone, diisopropyl ketone, and pinacolone were mixed with DIF in tetrahydrofuran, either α-phenyl or α,α-diphenyl ketones were produced and isolated in yields ranging from 20 to 88percent.That the regiochemistry of α-phenylation can be controlled by an appropriate choice of silyl enol ether was demonstrated with the kinetic and thermodynamic silyl enol ethers of 2-methylcyclohexanone, the thermodynamic silyl enol ether of 2-methylcyclopentanone, and the kinetic silyl enol ether of 2-pentanone. 3,3-Dimethyl-2-(silyloxy)-1-butene gave a dehydro dimer of pinacolone with DIF in addition to α-phenylpinacolone, thus suggesting that phenylations of silyl enol ethers with DIF may proceed via radical intermediates.
