Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• appears as a white solid. 1H NMR (400 MHz, 298 K, CDCl3) δ 7.35 (s, 3H), 4.45 (s, 6H) ppm. 1,3,5-Tribromo-2,4,6-trimethylbenzene (4b): The general procedure was adapted considering the three ring positions to be halogenated (3.5 equiv of NaBr were used instead of 2.33 equiv). The raw product appears as

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• ). The active catalytic species for the CuAAC reaction were generated by reducing copper(II) sulfate with sodium ascorbate according to literature procedures [66][67]. 2-Azido-1,3,5-trimethylbenzene (mesityl azide) was easily synthesized in a distinct, preliminary step through the Sandmeyer reaction of

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

• Hisanori Senboku,
• Mizuki Hayama and
• Hidetoshi Matsuno

Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

• Pt wire as an anode is critical and essential in the present electrochemical amidomethylation. When other substituted benzenes such as anisole, 1,2- and 1,4-dimethoxybenzenes, 1,2,3-trimethoxybenzene, and 1,3,5-trimethylbenzene were used as substrates in the electrochemical Friedel–Crafts-type

• amidoalkylation, the desired products were not obtained/detected by 1H NMR. In contrast, it was reported that anisole [9][11][23] and 1,3,5-trimethylbenzene [23] could react with acyliminium ions generated by the chemical [9][11] or cation pool method [23] to produce amidomethylated products. These results

AlBr₃-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles

• Yelizaveta Gorbunova,
• Dmitry S. Ryabukhin and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2021, 17, 2663–2667, doi:10.3762/bjoc.17.180

• NOESY correlations between the vinyl proton and the aromatic protons or methyl groups in neighboring aryl substituents (see Supporting Information File 1). However, the configuration of nitrile 2o was unclear. Benzene, o-, m-, p-xylenes, and 1,2,4-trimethylbenzene (mesitylene) were included in the

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• tetrachlorocuprate (Li2CuCl4) to produce the tripentenylbenzene derivative 4 in 45% yield. Alternatively, they have also prepared the same compound 4 starting from a simple and commercially available 1,3,5-trimethylbenzene (mesitylene) by using n-BuLi, and 4-bromo-1-butene in the presence of N,N,N′,N

Multiple threading of a triple-calix[6]arene host

• Veronica Iuliano,
• Roberta Ciao,
• Emanuele Vignola,
• Carmen Talotta,
• Patrizia Iannece,
• Margherita De Rosa,
• Annunziata Soriente,
• Carmine Gaeta and
• Placido Neri

Beilstein J. Org. Chem. 2019, 15, 2092–2104, doi:10.3762/bjoc.15.207

• Fisciano (Salerno), Italy 10.3762/bjoc.15.207 Abstract The synthesis of the triple-calix[6]arene derivative 6 in which three calix[6]arene macrocycles are linked to a central 1,3,5-trimethylbenzene moiety is reported. Derivative 6 is able to give multiple-threading processes in the presence of

• a central 1,3,5-trimethylbenzene moiety. We have shown that 6 is able to give multiple-threading processes in the presence of dipentylammonium or dibenzylammonium axles. The formation of pseudo[2]rotaxanes, pseudo[3]rotaxanes, and pseudo[4]rotaxanes in CDCl3 solution was ascertained by 1D and 2D NMR

Different reactivity of phosphorylallenes under the action of Brønsted or Lewis acids: a crucial role of involvement of the P=O group in intra- or intermolecular interactions at the formation of cationic intermediates

• Stanislav V. Lozovskiy,
• Alexander Yu. Ivanov and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1491–1504, doi:10.3762/bjoc.15.151

• Supporting Information File 1). Reactions of allene 1a with strongly donating arenes, 1,3,5-trimethylbenzene (mesitylene), 1,2,4-trimethylbenzene (pseudocumene), phenol, thiophenol, 1,3-dimethoxybenzene, 1,4-dimethoxybenzene, and other arenes, such as 1,2-dichlorobenzene, 1,4-dibromobenzene, gave rise to

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• , xylenes, 1,3,5-trimethylbenzene, 2,4-dichlorotoluene, and ethylbenzene. α-Acyloxy ethers 180 were synthesized by the oxidative coupling of benzyl alcohols 178 with ethers 179 (dioxane, tetrahydropyran, tetrahydrofuran, 1,2-dimethoxyethane) using Cu(OAc)2/t-BuOOH system [152] (Scheme 37). In a series of

(How) does 1,3,5-triethylbenzene scaffolding work? Analyzing the abilities of 1,3,5-triethylbenzene- and 1,3,5-trimethylbenzene-based scaffolds to preorganize the binding elements of supramolecular hosts and to improve binding of targets

• Xing Wang and
• Fraser Hof

Beilstein J. Org. Chem. 2012, 8, 1–10, doi:10.3762/bjoc.8.1

• 1,3,5-triethylbenzene template directs the binding elements toward the same face of the central ring, hence increasing the binding affinity. At the same time the 1,3,5-trimethylbenzene scaffold, without steric-gearing effects, has also been found to improve the binding affinities of hosts compared to

• methyl groups, but the size of this advantage can be small and is dependent on the groups involved. Keywords: binding affinity; entropy; molecular recognition; scaffolds; supramolecular hosts; triethylbenzene; trimethylbenzene; Introduction Supramolecular hosts use arrays of multiple weak interactions

• effect of 1,3,5-triethylbenzene-based hosts (1Et) has generally been demonstrated by comparing them to analogues that are unsubstituted at the 1,3,5 positions (1H). But a parallel set of literature reports describes structures (1Me) based on the 1,3,5-trimethylbenzene scaffold (700 structures in 300

An easy assembled fluorescent sensor for dicarboxylates and acidic amino acids

• Xiao-bo Zhou,
• Yuk-Wang Yip,
• Wing-Hong Chan and
• Albert W. M. Lee

Beilstein J. Org. Chem. 2011, 7, 75–81, doi:10.3762/bjoc.7.11

• -trimethylbenzene with sodium azide in DMSO afforded the corresponding bis-azide. Transformation of the crude bis-azide into bis-isothiocyanate 3 was achieved by treatment with triphenylphosphine in the presence of CS2. The “fluorophore–spacer–receptor” sensing motif for carboxylate was incorporated into the

• spectrofluorimeter. Unless otherwise specified, all fine chemicals were used as received. Synthesis of 2,4-bis(isothiocyanatomethyl)-1,3,5-trimethylbenzene (3): A mixture of 3,4-bis(bromomethyl)-1,3,5-trimethylbenzene (0.306 g, 1 mmol) and NaN3 (0.14 g, 2.2 mmol) in dry DMSO (30 mL) was stirred for 3 h at 50 °C

• (1:10) as eluent to give 3 as a white solid (200 mg, 76% yield). Its characterization data is in agreement with that reported [29]. Synthesis of 2-anthrancenylthioureamethyl-4-isothiocyanatomethyl-1,3,5-trimethylbenzene (4): Compound 3 (130 mg, 0.5 mmol) and anthrancen-9-yl-methanamine (110 mg, 0.5

Chain stopper engineering for hydrogen bonded supramolecular polymers

• Thomas Pinault,
• Bruno Andrioletti and
• Laurent Bouteiller

Beilstein J. Org. Chem. 2010, 6, 869–875, doi:10.3762/bjoc.6.102

• such as chloroform [22], carbon tetrachloride [28] and 1,3,5-trimethylbenzene [29]. The tube form contains three molecules in its cross section [6][30][31], and is the most stable structure at concentrations above 10−5mol/L and at room temperature, in solvents such as toluene [32] and dodecane [5

• supramolecular polymers. Therefore, we measured the viscosity of solutions of EHUT at a fixed concentration (20 mM) with increasing amounts of chain stopper. For this, 1,3,5-trimethylbenzene was chosen as the solvent because it is known to favor the formation of EHUT filaments at room temperature [29]. Figure 5

• temperature [32] and has a similar polarity as 1,3,5-trimethylbenzene. Figure 6 shows that all four compounds also reduce the relative viscosity of EHUT in toluene, but the situation is more complex than in trimethylbenzene. If we consider first the part of the curves with a stopper to monomer fraction lower