6786-36-3Relevant academic research and scientific papers
Acylative Suzuki coupling of amides: Acyl-nitrogen activation via synergy of independently modifiable activating groups
Li, Xijing,Zou, Gang
, p. 5089 - 5092 (2015/03/30)
A highly efficient palladium-catalyzed acylative cross-coupling of carboxylic amides with arylboronic acids has been achieved via synergistic activation of the Cacyl-N bond by independently modifiable activating groups. Coupling of amides features not only good functional group tolerance but also modifiable reactivities to overcome steric hindrance. This journal is
Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates
Li, Xijing,Zou, Gang
, p. 136 - 145 (2015/07/27)
Abstract A general and efficient acylative Suzuki coupling of active amides with diarylborinic acids has been achieved by using 1 mol% Pd(PCy3)2Cl2/0.6 mol% PCy3 as catalyst system taking advantage of modifiable reactivities of acyl-nitrogen bonds of amides. Both electronic and steric influences from either aryl or acyl counterparts on the coupling proved to be negligible or small. A variety of aryl ketones including sterically hindered ones could be synthesized by the coupling of diarylborinic acids in good to excellent yields. Sodium tetraarylborates could also be used as high atom-economy aryl source in the palladium-catalyzed cross-coupling with active amides.
Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: Synthesis of alkyl aryl ketones
Yousuf, Md,Das, Tuluma,Adhikari, Susanta
, p. 8763 - 8770 (2015/11/10)
Palladium catalyzed acylation of arylboronic acid containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester.
Phase behavior and molecular packing of octadecyl phenols and their methyl ethers at the air/water interface
Peikert, Miroslawa,Chen, Xiadong,Chi, Lifeng,Brezesinski, Gerald,Janich, Simon,Wuerthwein, Ernst-Ulrich,Schaefer, Hans J.
, p. 5780 - 5789 (2014/06/10)
Noncovalent molecular interactions, such as hydrogen bonding and van der Waals forces, play an important role in self-assembling to supramolecular structures. To study these forces, we chose monolayers at the air/water interface to limit the possible arrangements of the interacting molecules. Furthermore, monolayers provide useful tools to understand and study interactions between molecules in a controlled and fundamental way. The phase behavior and molecular packing of the phenols 1-(4-hydroxyphenyl)-octadecane (5a), 1-(3,4-dihydroxyphenyl)-octadecane (6), and 1-(2,3,4-trihydroxyphenyl)- octadecane (3) and their methyl ethers in monolayers at the air/water interface have been examined by π/A isotherms, Brewster angle microscopy (BAM), grazing incidence X-ray diffraction (GIXD) measurements, and density functional theory (DFT) calculations. The phenols are synthesized by Friedel-Crafts acylation of methoxybenzenes, hydrogenation of the resulting aryl ketones, and cleavage of the aryl methyl ethers. In the π/A isotherms and in BAM, the phenols show patches of the solid condensed phase at large molecular areas and the monolayers collapse at high pressures. Furthermore, the dimensions of the unit cell obtained by GIXD measurements are compatible with an arrangement of the phenyl rings that allows one aryl ring to interact with four adjacent phenyl rings in an edge-to-face arrangement, which leads to a significant binding energy. The experimental data are in good agreement with DFT calculations of 2D crystalline benzene and p-cresol arrangements. The enhanced monolayer stability of phenol 5a can be explained by hydrogen bonds of the hydroxyl group with water and van der Waals forces between the alkyl chains and aryl-aryl interactions.
Liquid-crystalline polymorphism of symmetrical azobananas: Bis(4-(4-alkylphenyl)azophenyl) 2-nitroisophtalates
Zygadlo,Dardas,Nowicka,Hofmann,Galewski
scheme or table, p. 283 - 291 (2011/08/02)
In this paper we present a series of novel compounds, bis(4-(4-alkylphenyl) azophenyl) 2-nitroisophtalates, which exhibit nematic and banana-type liquidcrystalline phases. The alkyl chain length varies from 1 to 18 carbons. The first ten members of this series exhibit nematic phase. The last eleven compounds exhibit banana-type liquid crystalline phases. The propyl and pentyl derivatives have extra second type of banana mesophase. Copyright Taylor & Francis Group, LLC.
Type II Photochemistry of Ketones in Liquid Crystalline Solvents. The Influence of Ordered Media on Biradical Dynamics
Hrovat, David A.,Liu, Jerry H.,Turro, Nicholas J.,Weiss, Richard G.
, p. 7033 - 7037 (2007/10/02)
The Norrish type II photochemistry of five alkylphenones, PhCO(CH2)nH (1a, n=4; 1b, n=10; 1c, n=17; 1d, n=19; 1e, n=21), 10-nonadecanone (2), and 2-undecanone (3) was studied in the isotopic, smetic, and solid phases of n-butyl stearate.The ratio of elimination-to-cyclization products for ketones 1c-e and 2 exhibits a strong phase dependence with a 7-8-fold increase in the smectic phase relative to the isotropic phase.The ratio of isomeric cyclobutanols from 2 shows a similar change.Further increases in the elimination-to-cyclization ratio are observed for 1d in the solid phase.The product ratios for ketones 1a, 1b, and 3 are the same in all the phase studied.Transient absorption studies on the intermediate 1,4-biradical produced from laser flash photolysis of 1d yield lifetimes of 64 +/- 5 and 70 +/- 5 ns in the isotopic and smectic phases, respectively.These results are explaned in terms of the structures of the various phases of n-butyl stearate and the accepted behavior of Norrish type II biradicals.
