- 1,2-Disubstituted 1,2-Dihydro-1,2,4,5-tetrazine-3,6-dione as a Dynamic Covalent Bonding Unit at Room Temperature
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Dynamic covalent bonds are useful tools in a wide range of applications. Although various reversible chemical reactions have been studied for this purpose, the requirement for harsh conditions, such as high temperature and low or high pH, to activate generally stable covalent bonds limits their potential applications involving biomolecules or household utilization. Here, we report the design, synthesis, characterization, and dynamic covalent bonding properties of 1,2-disubstituted 1,2-dihydro-1,2,4,5-tetrazine-3,6-dione (TETRAD). Hetero-Diels–Alder reactions of TETRAD with furan derivatives and their retro-reactions proceeded rapidly at room temperature under neutral conditions, enabling a chemically induced sol–gel transition system.
- Ikeda, Kazuki,Kabasawa, Akira,Kakugo, Akira,Kawai, Kentaro,Kojima, Masahiro,Kokado, Kenta,Matsunaga, Shigeki,Sada, Kazuki,Sato, Akane,Yoshino, Tatsuhiko
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supporting information
p. 1370 - 1379
(2022/02/01)
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- A facile and mild Pd-catalyzed one-pot process for direct hydrodeoxygenation (HDO) phenols to arenes through a ArOSO2F intermediates transformation
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A practical one-pot process for hydrodeoxygenation (HDO) of phenolic derivatives to their corresponding arenes was developed. This method provided a facile route to upgrading bio-oil. The substrate scope of this protocol was wide, complicated and multi-phenolic compounds were also smoothly hydrodeoxygenated to their corresponding arenes.
- Wang, Xiao-Yan,Leng, Jing,Wang, Shi-Meng,Asiri, Abdullah M.,Marwani, Hadi M.,Qin, Hua-Li
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supporting information
p. 2340 - 2343
(2017/05/29)
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- OXACAZONE COMPOUNDS TO TREAT CLOSTRIDIUM DIFFICILE
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Compounds, compositions, and methods for treating C. difficile are provided.
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- Oxidative addition of a strained C-C bond onto electron-rich rhodium(I) at room temperature
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The C-C bond of cyclobutanones undergoes oxidative addition to a T-shape rhodium(I) complex possessing a PBP pincer ligand at room temperature. The remarkable propensity of the rhodium complex for oxidative addition is attributed to the highly electron-donating nature of the boron ligand as well as the unsaturation on the rhodium center.
- Masuda, Yusuke,Hasegawa, Maki,Yamashita, Makoto,Nozaki, Kyoko,Ishida, Naoki,Murakami, Masahiro
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supporting information
p. 7142 - 7145
(2013/06/27)
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- ALKYLAROMATICS PRODUCTION
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The present invention provides a process for producing a monoalkylated aromatic compound, particularly cumene, comprising the step of contacting a polyalkylated aromatic compound with an alkylatable aromatic compound under at least partial liquid phase co
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- Transformations of N-Substituted Benzotriazoles into the Corresponding Carbanions by C-Benzotriazole Bond Scission
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Various TV-substituted benzotriazoles are transformed, by scission of the C-benzotriazole bond, into the corresponding carbanions by treatment with lithium. Thus, N-(diphenylmethyl)benzotriazole (1), N-benzylbenzotriazole (6), and N-allylbenzotriazole (10) all gave carbanions that reacted with diverse electrophiles to afford the corresponding products in good yields. This new methodology was successfully utilized to convert N-benzylbenzotriazole (6) and N-allylbenzotriazole (10) into dianion synthons by a sequential lithiation and reductive coupling and bis(benzotriazolyl)toluene (18) by double reductive couplings, demonstrating the synthetic potential of the present methodology.
- Katritzky, Alan R.,Qi, Ming
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p. 4116 - 4120
(2007/10/03)
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- Process for the preparation of aromatic dicarboxylic acids and aromatic hydrocarbons
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Aromatic dicarboxylic acids of the formula STR1 in which R1, R2, m, n, and X have the meaning mentioned in the description, can be prepared from the bisphenols, on which they are based, of the formula STR2 if the bisphenols are first reacted to give the bissulphonates, the sulphonate groups are removed catalytically with H2 and the hydrocarbons obtained in this way are doubly acylated in a known manner and the acyl groups are oxidized to the carboxyl groups. Many of the aromatic dicarboxylic acids which can be prepared in this way are new.
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- Process for the preparation of geminal diarylalkanes, new geminal diarylalkanes and alk(en)ylated aromatic compounds
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The invention relates to a new process for the preparation of geminal diarylalkanes of the formula STR1 by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl4 , to α-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
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- Regioselective nitration of diphenyl compounds
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A regioselective nitration process for diphenyl compounds which can be carried out at about ambient temperature in which each ring of the diphenyl compound is selectively nitrated in the para position to form the corresponding di(4-nitrophenyl) compound. Such compounds as diphenyl carbonate, 2,2-diphenylpropane, 2,2-diphenylhexafluoropropane, diphenyl sulfide, diphenyl ketone, diphenyl sulfone, and the like can be converted to an isomeric mixture containing an enhanced amount of the corresponding di(4-nitrophenyl) compound, which mixture may be reduced or purified and reduced to the di(4-aminophenyl) analogues for use in the manufacture of polyamides, polyimides, and polyamide-imides.
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- Influence of Solvent and Cation on the Properties of Oxygen-containing Organic Anions. Part 4. Mechanism and Reactivity of Tetraaryloxirane Cleavage with Alkali Metals
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Six tetraaryloxiranes 1a-f (Scheme 4) were reduced (Schemes 1-3) with alkali metals (M = Li, Na, K, Cs) in eight polar aprotic solvents under an inert atmosphere.The organometallic solutions thus obtained were hydrolysed and the reaction products analysed.Similar experiments were carried out where the same solutions were quenched with D2O or MeI.In some cases the same solutions were studied by NMR and ESR spectroscopy before quenching.A stepwise reduction mechanism was established where the transfer of a first electron produces CO-bond scission in the oxirane ring, yielding a short-lived radical anion 4 or 5 (Scheme 1), i. e., a tetraalkyl-β-oxidoethyl radical.This intermediate can either eliminate oxygen as metal oxide (MO) to produce a tetraarylethylene 24 (Scheme 2) or be further reduced to a dianion 8 or 9 (Scheme 1).This anion yields, upon hydrolysis, low yields,if any, of the corresponding tetraphenylethanol 15 or 16 (Z = H).The larger proportion of the dianion, after the first protonation step, yielding anion 11 or 22, undergoes CC-bond scission which leads eventually to the corresponding ketone and diarylmethane 19 + 20 or 21 + 23 (Z = H) (Scheme 2).Other possible pathways were excluded through experiments where other possible intermediates were generated.These led to different end products.A triparametric linear correlation as a function of solvent parameters ETN and DN, as well as the cationic radius, was established for the influence of the nature of the solvent and counter-ion on the ratio between the rates of formation of products stemming from metal oxide (MO) elimination by the ring-opened radical anion 4 or 5 (Schemes 1 and 2) and rates of formation of products stemming from further reduction of the same radical anion to the dianion 8 or 9, thus confirming the mechanism established.
- Franco, M. Luisa T. M. B.,Herold, Bernardo J.,Maercker, Adalbert
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p. 119 - 129
(2007/10/02)
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- Conversion of aromatic ketones, benzyl alcohols, and alkyl aryl ethers to aromatic hydrocarbons with lithium 4,4'-di-t-butylbiphenyl radical anion
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Treatment of tetrahydrofuran (THF) solutions of the title compounds with excess lithium (or potassium) metal under ultrasonic irradiation in the presence of catalytic amounts of the electron-transfer agent 4,4'-di-t-butylbiphenyl (DBB) caused conversions to aromatic hydrocarbons in good yields. Addition of 1 or 2 equiv of alkyl halides prior to aq ammonium chloride treatment during workup provided mono- or di-alkylated products.
- Karaman,Kohlman,Fry
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p. 6155 - 6158
(2007/10/02)
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- NITRO COMPOUNDS AS ALKYLATING REAGENTS IN FRIEDEL-CRAFTS CONDITIONS REACTION OF 2-NITROPROPANE WITH BENZENE
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Friedel-Crafts reaction of benzylic or tertiary nitro compounds with benzene gave normal alkylation products.Similarly, 2-nitropropane (2-NP) gave cumene (1) which underwent further transformation affording a mixture whose behaviour with time was investigated: results were consistent with oxidative formation of the cumyl carbonium ion (7').
- Bonvino, V.,Casini, G.,Ferappi, M.,Cingolani, G. M.,Pietroni, B. R.
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p. 615 - 620
(2007/10/02)
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- Direct Geminal Dimethylation of Ketones using Dimethyltitanium Dichloride
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Ketones are readily converted into the corresponding geminal dimethyl derivatives on reaction with dimethyltitanium dichloride under mild conditions; tertiary alcohols react similarly.
- Reetz, Manfred T.,Westermann, Juergen,Steinbach, Rainer
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p. 237 - 239
(2007/10/02)
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