13074-65-2Relevant academic research and scientific papers
One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst
Xue, Weiyang,Gu, Bin,Wu, Huiling,Liu, Mengyang,He, Songbo,Li, Jingmei,Rong, Xin,Sun, Chenglin
, (2021/03/26)
2-Alkyl cycloketones are essential chemicals and intermediates for synthetic perfumes and pesticides, which are conventionally produced by multistep process including aldol condensation, separation and hydrogenation. In present work, a batch one-pot cascade approach using aldehydes and cycloketones as the raw materials, and a bifunctional Pd/ZrO2 catalyst was developed for the synthesis of 2-alkyl cycloketones, e.g., cyclohexanone and cycloheptanone. Very high aldehydes (except for paraldehyde with large steric hindrance) conversion and high yields for 2-alkyl cycloketones (e.g., 99 % of conversion for n-butanal and 76 wt.% of yield for 2-butyl cyclohexanone) were obtained at mild temperature of 140 °C. After 10 cycles of reuse, Pd/ZrO2 catalyst showed slight deactivation (ca. 5 % conversion and 10 % yield losses), due to the coke on the catalyst. However, the performance of the catalyst was completely recovered after an oxidative regeneration.
Kinetic Patterns of Condensation of Alkyl- and Cycloalkylcyclopentanones with Dihydric Alcohols in the Presence of Polyoxomolybdate Modified with Oxides of Rare-Earth Elements
Alimardanov, Kh. M.,Velieva,Dadashova
, p. 1882 - 1889 (2019/02/24)
The results of condensation of C5–C7 alkyl- and cycloalkyl-substituted cyclopentanones with diatomic vicinal alcohols in the presence of polyoxomolybdate modified with gadolinium oxide are considered. Kinetic patterns are investigated and a kinetic model of the process is proposed. It was established that alkyl- and cycloalkyl derivatives of dioxaspironone are formed directly by two parallel-consecutive routes and through the stages of the preparation of the corresponding hemiacetal. The ratio of the rate constants of these routes depends on the composition and structure of the starting ketones and diols.
Regioselective ketone α-alkylation with simple olefins via dual activation
Mo, Fanyang,Dong, Guangbin
, p. 68 - 72 (2014/07/21)
Alkylation of carbonyl compounds is a commonly used carbon-carbon bond-forming reaction. However, the conventional enolate alkylation approach remains problematic due to lack of regioselectivity, risk of overalkylation, and the need for strongly basic conditions and expensive alkyl halide reagents. Here, we describe development of a ketone-alkylation strategy using simple olefins as the alkylating agents. This strategy employs a bifunctional catalyst comprising a secondary amine and a low-valent rhodium complex capable of activating ketones and olefins simultaneously. Both cyclic and acyclic ketones can be mono-a-alkylated with simple terminal olefins, such as ethylene, propylene, 1-hexene, and styrene, selectively at the less hindered site; a large number of functional groups are tolerated.The pH/redox neutral and byproduct-free nature of this dual-activation approach shows promise for large-scale syntheses.
Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones
Morisson,Barnier,Blanco
, p. 7749 - 7764 (2007/10/03)
Optically active α-methyl α-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives.
Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones
Abbasov,Alimardanov,Suleimanova
, p. 621 - 626 (2007/10/03)
Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.
Conversion of 2-alkylcyclopentanones into 2-alkyl-2-cyclopentenones with hydrated ferric chloride and cupric chloride
Cardinale, G.,Laan, J. A. M.,Russel, S. W.,Ward, J. P.
, p. 199 - 202 (2007/10/02)
Hydrated ferric chloride, FeCl3*6H2O, in a polar, hydroxylic solvent converted 2-alkylcyclopentanones directly into 2-alkyl-2-cyclopentenones on heating in the presence of air.Yields of isolated products were about 40 percent.The scope of the reaction is discussed.With cupric chloride, chloroketones were formed as intermediates, which could be dehydrochlorinated to 2-alkyl-2-cyclopentenones in similar yields.
