294-62-2Relevant articles and documents
A novel reaction in ionic liquids: Selective cyclization of 1-dodecene to cyclododecane under moderate pressure
Qiao, Kun,Deng, Youquan
, p. 2191 - 2193 (2003)
A novel reaction of cyclization of 1-dodecene to cyclododecane with high selectivity, especially under moderate pressure, is found in ethanol buffered chloroaluminate ionic liquids with easy separation of product due to the immiscibility with ionic liquids.
Diastereomeric cyclic tris-allenes
Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.
, p. 2497 - 2499 (2013)
Both diastereomers of the tris-allene, cyclododeca-1,2,5,6,9,10-hexaene have been obtained using a triple cyclopropylidene-allene rearrangement. On the NMR timescale, one has D3 symmetry, and is the smallest hydrocarbon synthesised to have this symmetry, and the second has C2 symmetry.
5,10-Dihydro-Silanthrene as a Reagent for the Barton-McCombie Reaction
Gimisis, T.,Ballestri, M.,Ferreri, C.,Chatgilialoglu, C.,Boukherroub, R.,Manuel, G.
, p. 3897 - 3900 (1995)
The deoxygenation of secondary alcohols via thionoesters with the use of 5,10-dihydrosilanthrene as the radical reducing agent has been studied in detail.The ability of hydrogen donation of this silane has been measured using the one-carbon ring expansion of 1-(2-oxocyclopentyl)ethyl radical as a timing device.
Discrimination of Rotational Isomeric States in Cycloalkanes by Solid-State CP-MAS 13C NMR Spectroscopy
Moeller, Martin,Gronski, Wolfram,Cantow, Hans Joachim,Hoecker, Hartwig
, p. 5093 - 5099 (1984)
The solid-state behavior of three cycloalkanes, cyclododecane, cyclotetraeicosane, and cyclohexatriacontane, was investigated by means of temperature dependent magic angle cross-polarization 13C NMR experiments.For the two smaller ring molecules a state of high internal mobility like the "rotator phase" in n-alkanes was detected.It could be correlated with a phase transition in the solid state visible by means of DSC.In the case of (CH2)12 this is 151 K below the melting point, and in the case of (CH2)24 it is 25 K below the melting transition.The CP-MAS 13C NMR spectra show a transition from the fast exchange to the slow exchange regime of magnetically nonequivalent states.By comparison with X-ray diffraction data the well-resolved resonance signals for the low-temperature phases were assigned to molecular segments distinguished by the rotational isomeric states of the carbon-carbon bonds.Chemical shift differences due to conformational isomerism were as large as 12 ppm; thus, they exceed "packing effects" by far.
Flow Chemistry under Extreme Conditions: Synthesis of Macrocycles with Musklike Olfactoric Properties
Seemann, Alexandra,Panten, Johannes,Kirschning, Andreas
supporting information, p. 13924 - 13933 (2021/05/29)
Starting from small cyclic ketones, continuous flow synthesis is used to produce medium-sized rings and macrocycles that are relevant for the fragrance industry. Triperoxides are important intermediates in this process and are pyrolyzed at temperatures above 250 °C. The synthesis is carried out in two continuously operated flow reactors connected by a membrane-operated separator. The practicality of flow chemistry is impressively demonstrated in this work by the use of hazardous reagent mixtures (30% H2O2, 65% HNO3) and the pyrolysis of no less problematic peroxides. All new macrocycles were tested for their olfactory properties in relation to musk.
A New Protocol for Catalytic Reduction of Alkyl Chlorides Using an Iridium/Bis(benzimidazol-2′-yl)pyridine Catalyst and Triethylsilane
Fukuyama, Takahide,Hamada, Yuki,Ryu, Ilhyong
, p. 3404 - 3408 (2021/07/14)
The reduction of alkyl chlorides using triethylsilane is investigated. Primary, secondary, tertiary, and benzylic C-Cl bonds are effectively converted into C-H bonds using an [IrCl(cod)] 2/2,6-bis(benzimidazol-2′-yl)pyridine catalyst system. This catalyst system is quite simple since the tridentate N-ligand can be easily prepared in one step from commercially available reagents.
Sustainable System for Hydrogenation Exploiting Energy Derived from Solar Light
Ishida, Naoki,Kamae, Yoshiki,Ishizu, Keigo,Kamino, Yuka,Naruse, Hiroshi,Murakami, Masahiro
supporting information, p. 2217 - 2220 (2021/02/16)
Herein described is a sustainable system for hydrogenation that uses solar light as the ultimate source of energy. The system consists of two steps. Solar energy is captured and chemically stored in the first step; exposure of a solution of azaxanthone in ethanol to solar light causes an energy storing dimerization of the ketone to produce a sterically strained 1,2-diol. In the second step, the chemical energy stored in the vicinal diol is released and used for hydrogenation; the diol offers hydrogen onto alkenes and splits back to azaxanthone, which is easily recovered and reused repeatedly for capturing solar energy.
Hydrogenation of 1,5,9-Cyclododecatriene in a Three-Phase System in the Presence of Nickel Nanoparticles Supported on NаX Zeolite
Nebykov,Popov, Yu. V.,Mokhov,Shcherbakova,Zotov, Yu. L.
, p. 110 - 115 (2021/03/18)
The hydrogenation of 1,5,9-cyclododecatriene in the presence of nanostructured Ni catalysts, supported with NaX zeolite, in a flow-through reactor at atmospheric hydrogen pressure was investigated. Nickel nanoparticles on the support surface were prepared by chemical reduction of the precursor (NiCl2) with NaBH4 and NH2NH2. The effect exerted on the yield of hydrogenation products by the nominal residence time of the gas phase in the reaction zone and by the process temperature was considered, and the catalyst operation life was analyzed. The catalysts showed high activity and allowed preparation of cyclododecane in ~100% yield at a process temperature of up to 160°С.
Method for hydrogenolysis of halides
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Paragraph 0232; 0239-0241, (2021/01/11)
The invention discloses a method for hydrogenolysis of halides. The invention discloses a preparation method of a compound represented by a formula I. The preparation method comprises the following step: in a polar aprotic solvent, zinc, H2O and a compound represented by a formula II are subjected to a reaction as shown in the specification, wherein X is halogen; Y is -CHRR or R; hydrogenin H2O exists in the form of natural abundance or non-natural abundance. According to the preparation method, halide hydrogenolysis can be simply, conveniently and efficiently achieved through a simple and mild reaction system, and good functional group compatibility and substrate universality are achieved.
4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent
Kobayashi, Shoji,Tamura, Tomoki,Yoshimoto, Saki,Kawakami, Takashi,Masuyama, Araki
, p. 3921 - 3937 (2019/11/11)
4-Methyltetrahydropyran (4-MeTHP) is a hydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, a comprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests 4-MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4-MeTHP was found incompatible with strong Lewis acids, and the C?O bond was readily cleaved by treatment with BBr3. Moreover, the radical-based degradation pathways of 4-MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chemistry perspectives.
