41997-44-8Relevant academic research and scientific papers
Electron-Deficient Chiral Lactic Acid-Based Hypervalent Iodine Reagents
Qurban, Jihan,Elsherbini, Mohamed,Wirth, Thomas
, p. 11872 - 11876 (2017/11/24)
Novel electron-deficient chiral hypervalent iodine reagents were prepared in good overall yields. The reactivity and stereoselectivity of these reagents in oxidative rearrangements of alkenes to α-aryl ketones were investigated. The results show that the new reagents have good reactivity and generate products with high enantiomeric excess.
Intermolecular Reductive Cross Coupling of Carbonyl Compounds with Nitriles Induced by Low-valent Titanium
Gao, Ju,Hu, Ming-yang,Chen, Jian-xie,Yuan, Su,Chen, Wei-xing
, p. 1617 - 1620 (2007/10/02)
Intermolecular cross coupling of carbonyl compounds with nitriles promoted by TiCl4-Zn leads to ketones.
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.
Formation and Reactions of 1-Phenyl-2-propanone Dianion and Related Systems with Electrophilic Reagents
Trimitsis, G. B.,Hinkley, J. M.,TenBrink, R.,Faburada, A. L.,Anderson, R.,et al.
, p. 2957 - 2962 (2007/10/02)
1-Phenyl-2-propanone, 1,1-diphenyl-2-propanone, and 1-(4-methoxyphenyl)-2-propanone were converted to their dicarbanions 3, 4, and 31, respectively, and their reactions with a number of electrophilic reagents were examined.All three dianions gave a mixture of C-1 and C-3 alkylation products when treated with alkyl halides of higher reactivity, while only C-1 alkylations occurred when alkyl halides of lower reactivity were used.It was also found that the 1,1-diphenyl-2-propanone and the 1-(4-methoxyphenyl)-2-propanone dianions 4 and 31 gave a higher ratio of C-1/C-3 alkylation products than the 1-phenyl-2-propanone dianion 3.When dianion 3 was reacted with p-anisaldehyde and a number of protonating agents, electrophilic attack occurred exclusively at the C-3 position.The trends observed are analyzed, and mechanisms are proposed to account for the results obtained.
