21173-96-6Relevant academic research and scientific papers
Mechanofluorochromism of NIR-emitting dyes based on difluoroboron β-carbonyl cyclic ketonate complexes
Zhang, Fushuang,Zhai, Lu,Feng, Siwei,Mi, Wenhua,Sun, Jingbo,Sun, Meng,Zhao, Jinyu,Lu, Ran
, p. 140 - 148 (2018)
New difluoroboron β-carbonyl cyclic ketonate complexes CnB (n = 2, 16), in which carbazole was linked to difluoroboron β-diketonate directly, and DCnB (n = 2, 16), where two terminal carbazole units were bridged by vinyl groups to link to difluoroboron β-
Tautomerization of 2-acetylcyclohexanone in assemblies of cationic surfactants
Iglesias, Emilia
, p. 457 - 464 (2005)
The kinetic study of the keto-enol interconversion of 2-acetylcyclohexanone (ACHE) has been performed in organic solvents such as dimethylsulfoxide, 1-propanol, 2-propanol, methanol, dioxane, tetrahydrofuran and acetonitrile, as well as in aqueous micella
Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
Miyagi, Toshinori,Okada, Sho,Tada, Naoya,Sugihara, Masahiro,Kagawa, Natsuko,Takabatake, Tetsuhiko,Toyota, Masahiro
supporting information, p. 1653 - 1657 (2019/05/29)
A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification.
A New Route to Phenols: Palladium-Catalyzed Cyclization and Oxidation of γ,δ-Unsaturated Ketones
Samadi, Sadaf,Orellana, Arturo
, p. 2472 - 2475 (2016/08/25)
We report a new strategy for the synthesis of phenols from acyclic unsaturated ketones in one pot. The reaction proceeds by palladium-catalyzed carbopalladation of an alkene with the enol form of the tethered ketone, generating a substituted cyclohexanone. Upon introduction of a terminal oxidant a palladium-catalyzed oxidation ensues to give the desired phenol. This approach allows the programming of phenol substituents on the acyclic substrate and therefore circumvents the limitations inherent in traditional syntheses of phenols.
Solvent effects versus concentration effects in determining rates of base-catalyzed keto-enol tautomerization
Iglesias, Emilia
, p. 625 - 632 (2007/10/03)
Solvent effects of homogeneous media (such as solvent-water mixtures) on chemical reactivity may be interpreted as due to solvent polarity and/or molecular structure of solvent molecules. In microheterogeneous media (such as aqueous micellar solutions), solvent effects on reaction rates must include concentration effects, in addition to changes in the solvent polarity of the micelle interface where the reaction is assumed to occur. In this work, we measured the rates of keto-enol tautomerization of the 2-acetylcyclohexanone (ACHE) and 2-acetyl-1-tetralone (ATLO) systems in dimethylsulfoxide (DMSO)-water mixtures and in aqueous micellar solutions with both anionic and cationic surfactants and in the presence of buffers. The results appear as an ideal framework to understand the paramount importance of the specific molecular structure of solvent molecules in determining chemical reactivity versus solvent polarity or even concentration effects. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
Tautomerization of 2-acetylcyclohexanone. 1. Characterization of keto-enol/enolate equilibria and reaction rates in water
Iglesias, Emilia
, p. 2680 - 2688 (2007/10/03)
The keto-enol tautomerism of 2-acetylcyclohexanone (ACHE) was studied in water under different experimental conditions. By contrast with other previously studied β-diketones, the keto-enol interconversion in the ACHE system is a slow process. Under equilibrium conditions, the analysis of the absorbance readings of ACHE aqueous solutions yielded more than 40% of enol content at 25 °C; nevertheless, in aprotic solvents such as dioxane, ACHE is almost completely enolized. In alkaline medium, the enolate ion is the only existing species; the study of the effect of pH on the UV-absorption spectrum of ACHE yielded a value of 9.85 for the overall pKa of ACHE. Under nonequilibrium conditions, the keto-enol tautomerization was studied in water. Several factors affecting the reaction have been investigated, which include H+-catalysis, ionic strength effect, buffer catalysis, deuterium isotope effects, temperature effect, or solvent effects.
REACTION OF 2-ACETYL-2-CYCLOALKEN-1-ONES WITH CYCLIC β-DIKETONES
Akhrem, A. A.,Lakhvich, F. A.,Pyrko, A. N.
, p. 2027 - 2033 (2007/10/02)
The corresponding 2-acetyl-1,3-cyclohexadien-1-ols were obtained by the reduction of 2-acetyl-3-chloro-2-cyclohexen-1-one and 2-acetyl-3-chloro-5,5-dimethyl-2-cyclohexen-1-one with zinc activated by silver acetate.They were studied in the Michael addition reaction with dimedone and 1,3-cyclohexanedione in the presence of sodium methoxide.It was concluded that the transformation of these 2-acetyl-2-cyclohexen-1-ones into the corresponding 2-acetyl-1,3-cyclohexadien-1-ols is reversible.By dehydration of the Michael addition adducts and reaction with ammonia tricycliccompounds with an additional pyran or dihydropyridine ring were obtained.
