84839-88-3Relevant academic research and scientific papers
β-Diazocarbonyl Compounds: Synthesis and their Rh(II)-Catalyzed 1,3 C?H Insertions
Jiang, Liyin,Wang, Zhaofeng,Armstrong, Melanie,Suero, Marcos G.
supporting information, p. 6177 - 6184 (2021/02/01)
Herein, we describe the first electrophilic diazomethylation of ketone silyl enol ethers with diazomethyl-substituted hypervalent iodine reagents that gives access to unusual β-diazocarbonyl compounds. The potential of this unexplored class of diazo compounds for the development of new reactions was demonstrated by the discovery of a rare Rh-catalyzed intramolecular 1,3 C?H carbene insertion that led to complex cyclopropanes with excellent stereocontrol.
Activity of antifungal organobismuth(III) compounds derived from alkyl aryl Ketones against S. cerevisiae: Comparison with a heterocyclic bismuth scaffold consisting of a diphenyl sulfone
Murafuji, Toshihiro,Tomura, Mai,Ishiguro, Katsuya,Miyakawa, Isamu
, p. 11077 - 11095 (2014/10/15)
A series of hypervalent organobismuth(III) compounds derived from alkyl aryl ketones [XBi(5-R′C6H3-2-COR)(Ar)] was synthesized to investigate the effect of the compounds' structural features on their antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to bismuth heterocycles [XBi(5-RC6H3-2-SO 2C6H4-1′-)] derived from diphenyl sulfones, a systematic quantitative structure-activity relationship study was possible. The activity depended on the Ar group and increased for heavier X atoms, whereas lengthening the alkyl chain (R) or introducing a substituent (R′) reduced the activity. IBi(C6H4-2-COCH 3)(4-FC6H4) was the most active. Its activity was superior to that of the related acyclic analogues ClBi[C6H 4-2-CH2N(CH3)2](Ar) and ClBi(C 6H4-2-SO2 tert-Bu)(Ar) and also comparable to that of heterocyclic ClBi(C6H4-2-SO2C 6H4-1′-), which was the most active compound in our previous studies. Density function theory calculations suggested that hypervalent bismuthanes undergo nucleophilic addition with a biomolecule at the bismuth atom to give an intermediate ate complex. For higher antifungal activity, adjusting the lipophilicity-hydrophilicity balance, modeling the three-dimensional molecular structure around the bismuth atom, and stabilizing the ate complex appear to be more important than tuning the Lewis acidity at the bismuth atom.
Highly stereoselective oxazaborolidinium ion catalyzed synthesis of (Z)-silyl enol ethers from alkyl aryl ketones and trimethylsilyldiazomethane
Kang, Byung Chul,Shim, Su Yong,Ryu, Do Hyun
supporting information, p. 2077 - 2079 (2014/05/06)
Highly stereoselective (Z)-silyl enol ethers were prepared from alkyl aryl ketones and trimethylsilyldiazomethane (TMSD) using an oxazaborolidinium ion catalyst. In addition, ring-expanded silyl enol ethers were successfully constructed from cyclic ketones. Their synthetic utilities were shown by sequential Mukaiyama aldol and [2 + 2]-cycloaddition reactions.
Mechanism of Arylation of Nucleophiles by Aryllead Triacetates. Part 2. Support for a Ligand Coupling Process and X-Ray Molecular Structure of (p-Methoxyphenyl)-α-methylphenacyllead(IV) Diacetate
Morgan, Jacqueline,Buys, Irmi,Hambley, Trevor W.,Pinhey, John T.
, p. 1677 - 1682 (2007/10/02)
In the presence of boron trifluoride-diethyl ether complex p-methoxyphenyllead triacetate 4 and the propiophenone silyl enol ether 6 were found to undergo a rapid reaction to give (p-methoxyphenyl)-α-methylphenacyllead diacetate 9 in high yield.Analogous products, 5, 10 and 11, respectively, were formed when the silyl enol ethers of acetophenone, butyrophenone and isobutyrophenone were treated under the same conditions with aryllead compound 4.The diorganolead diacetates 9, 10 and 11 were relatively unstable, giving a number of products when heated at 60 deg C in chloroform.In each case there was significant elimination of Pb(OAc)2, with formation of the product of ligand coupling, the deoxybenzoin. α-Methylphenacyl(o-prop-2-enyloxy)phenyllead diacetate 21, which was produced to probe the mechanism of the coupling reaction, behaved similarly to compound 9, giving no dihydrobenzofuran derivatives.Therefore, it would appear that aryl free radicals are most probably not produced in these thermal reactions, and a ligand-coupling mechanism is proposed.
