1610-39-5Relevant academic research and scientific papers
The Direct Production of Tri- and Hexa-Substituted Benzenes from Ketones under Mild Conditions
Elmorsy, Saad S.,Pelter, Andrew,Smith, Keith
, p. 4175 - 4176 (1991)
Treatment of aryl methyl ketones with tetrachlorosilane in ethanol gives good yields of 1,3,5-triarylbenzenes.Triannulated benzenes result from cyclopentanone and cyclohexanone.
Highly efficient synthesis of substituted benzenes in the presence of B(HSO4)3 as a new and reusable catalyst under solvent-free conditions
Safaei, Hamid Reza,Davoodi, Mansooreh,Shekouhy, Mohsen
, p. 2178 - 2190 (2013)
A highly efficient and simple procedure for the synthesis of substituted benzenes is described. A broad range of ketones (alkyl-aryl ketones and cyclic ketones) were condensed via a cyclotrimerization reaction in the presence of catalytic amounts of boron sulfonic acid [B(HSO4)3], a new, highly efficient, and reusable catalyst, under solvent-free conditions. All reactions completed in short times without formation of any by-products. The catalyst was recovered and reused successfully for 15 cycles of the reaction. Copyright
Synthesis of 1,4,5,8,9,12-hexabromododecahydrotriphenylene and its application in constructing polycyclic thioaromatics
Wei, Junfa,Jia, Xiaowei,Yu, Jun,Shi, Xianying,Zhang, Congjie,Chen, Zhanguo
, p. 4714 - 4716 (2009)
A new route for constructing PAHs from cyclohexanone by trimerization, bromination, trisannulation and aromatization, and the synthesis of a novel sulfur-containing polycyclic heteroaromatic have been described. The Royal Society of Chemistry 2009.
Triple self-condensation of ketones yielding aromatics promoted with titanium tetrachloride
Li,Sun,Jin,Shao
, p. 1947 - 1949 (2001)
Triple self-condensation of ketones was promoted by titanium tetrachloride in toluene to afford corresponding benzene derivatives, and the structure of tri(2-naphthyl)benzene was confirmed by X-ray single crystal diffraction.
Novel method for the synthesis of 1,3,5-triarylbenzenes from ketones
Jing, Xiaobi,Xu, Feng,Zhu, Qihua,Ren, Xinfeng,Yan, Chaoguo,Wang, Li,Wang, Jinrong
, p. 3167 - 3171 (2005)
Treatment of aryl ketones with p-toluenesulfinic acid and a catalytic amount of tin tetrachloride anhydrous (5%) in 1-pentanol gives good yields of 1,3,5-triarylbenzenes. Copyright Taylor & Francis, Inc.
Selective catalytic hydrogenation of polycyclic aromatic hydrocarbons promoted by ruthenium nanoparticles
Bresó-Femenia, Emma,Chaudret, Bruno,Castillón, Sergio
, p. 2741 - 2751 (2015/05/27)
Ru nanoparticles stabilised by PPh3 are efficient catalysts for hydrogenation of polycyclic aromatic hydrocarbons (PAHs) containing 2-4 rings under mild reaction conditions. These compounds were partially hydrogenated with good to excellent selectivities just by optimizing the reaction conditions. The influence of the nature of substituents present in different positions of naphthalene on the selectivity of hydrogenation was also studied. Hydrogenation of products containing substituents at position 1 is slower than that of products containing substituents at position 2. In all cases, hydrogenation takes place mainly on the less substituted ring.
H6P2W18O62/Nanoclinoptilolite as an efficient nanohybrid catalyst in the cyclotrimerization of aryl methyl ketones under solvent-free conditions
Tayebee,Jarrahi
, p. 21206 - 21214 (2015/04/14)
A new type of nanohybrid material H6P2W18O62/nanoclinoptilolite was fabricated and performed as an efficient and reusable catalyst in the mild and one-pot condensation of different acetophenones. The operational simplicity, easy work-up, cost-effective, and solvent-free nature of the present methodology were accompanied with good to excellent yields of the desired 1,3,5-triarylbenzenes from a wide range of alkyl, aryl, and cyclic ketones. The nanocatalyst was prepared via immobilization of Wells-Dawson heteropolyacid H6P2W18O62 (HPA) on the surface of nanoclinoptilolite (NCP). The nanohybrid material was easily recovered and reused successfully at least seven times without significant loss of catalytic activity. XRD, SEM, UV-Vis, MS-ICP, DTA, and FT-IR studies confirmed that the heteropolyacid is well dispersed on the surface of NCP. This protocol developed is a safe and convenient alternate method for the synthesis of 1,3,5-triarylbenzenes utilizing an eco-friendly and a highly reusable natural nanocatalyst. Furthermore, water was the only by-product, which made the present methodology environmentally benign.
A new method for the preparation of 1,3,5-triarylbenzenes catalyzed by nanoclinoptilolite/HDTMA
Tayebee,Jarrahi,Maleki,Kargar Razi,Mokhtari,Baghbanian
, p. 10869 - 10877 (2015/02/05)
A new natural surface modified nanoclinoptilolite (NCP) was prepared and applied as an efficient catalyst for the cyclotrimerization of acetophenones to obtain 1,3,5-triarylbenzenes. The results showed that the efficiency of this catalytic system was enhanced due to the surface modification by hexadecyltrimethylammonium bromide (HDTMA-Br). This proposed protocol brings about significant economic and environmental advantages, such as operational simplicity, short reaction time, mild reaction conditions, good reaction yield, and high recyclability of the catalyst. Furthermore, the only side product of the reaction is water, which makes this methodology an environmentally friendly process.
Highly selective self-condensation of cyclic ketones using MOF-encapsulating phosphotungstic acid for renewable high-density fuel
Deng, Qiang,Nie, Genkuo,Pan, Lun,Zou, Ji-Jun,Zhang, Xiangwen,Wang, Li
supporting information, p. 4473 - 4481 (2015/08/11)
Transferring biomass-derived cyclic ketones such as cyclopentanone and cyclohexanone to a mono-condensed product through aldol self-condensation has great potential for the synthesis of a renewable high-density fuel. However, the selectivity is low for numerous catalysts due to the rapid formation of di-condensed by products. Herein, MIL-101-encapsulating phosphotungstic acid is synthesized to catalyze the self-condensation with selectivity of more than 95%. PTA clusters are uniformly dispersed in MOF cages and decrease the empty space (pore size), which provides both acidic sites and shape-selective capability. The optimal PTA amount decreases corresponding to the increase of reactant size. The shape-selectivity is also realized by changing the pore size of MOF such as from MIL-101 to MIL-100. Moreover, the catalyst is resistant to PTA leaching and performs stably after 5 runs. After hydrodeoxygenation of the mono-condensed product, high-density biofuels with densities of 0.867 g ml-1 and 0.887 g ml-1 were obtained from cyclopentanone and cyclohexanone, respectively. This study not only provides a promising route for the production of high-density biofuel but also suggests the advantage of MOF-based catalysts for shape-selective catalysis involving large molecular size.
Mass spectrometric studies of self-condensation products of cyclohexanone under alkaline conditions and synthesis of dodecahydrotriphenylene and triphenylene from easily available reactants
Kovalev,Kopchuk,Zyryanov,Khasanov,Rusinov,Chupakhin
, p. 1539 - 1542 (2015/03/14)
LC-MS was used to study products of cyclohexanone self-condensation under alkaline conditions. Improved methods (as compared to those described in the literature) for the preparation of dodecahydrotriphenylene and highly pure sublimed triphenylene were suggested based on the easily available and cheap reactants. Possible reasons of the low yield of the target dodecahydrotriphenylene in the step of oligomerization of cyclohexanone were identified.
