4832-16-0Relevant articles and documents
Ozonation of decalin as a model saturated cyclic molecule: A spectroscopic study
Bykov, Gennadii L.,Ershov, Boris G.,Krasovskiy, Vladimir G.,Kustov, Alexander L.,Kustov, Leonid M.,Panich, Nadezhda M.
, (2021/09/20)
Ozonolysis is used for oxidation of a model cyclic molecule-decalin, which may be consid-ered as an analog of saturated cyclic molecules present in heavy oil. The conversion of decalin exceeds 50% with the highest yield of formation of acids about 15–17%. Carboxylic acids, ketones/aldehydes, and alcohols are produced as intermediate products. The methods of UV-visible, transmission IR, at-tenuated total reflection IR-spectroscopy, NMR and mass-spectrometry were used to identify reaction products and unravel a possible reaction mechanism. The key stage of the process is undoubtedly the activation of the first C-H bond and the formation of peroxide radicals.
Catalytic oxidation of alcohols using Fe-bTAML and NaClO: Comparing the reactivity of Fe(V)O and Fe(IV)O intermediates
Jana, Sandipan,Thomas, Jithin,Sen Gupta, Sayam
, p. 476 - 482 (2018/11/23)
We demonstrate the selective oxidation of secondary alcohols and activated primary alcohols to their corresponding aldehydes or ketones using Fe-bTAML as the catalyst and sodium hypochlorite (NaClO) as the oxidant. Good to excellent yields of 80%–99% for the carbonyl compounds and turnover numbers up to ～500 was obtained with this catalytic system. The reactions are clean, performed under mild conditions (air, room temperature) and yielded sodium chloride as the only by-product. The yield and turnover number were dependent on the pH of the reaction and this difference was attributed to the different reactive intermediates that was formed at pH 7 and pH 12 (FeV(O) and FeIV(O) respectively). Reactions involving the FeV(O) intermediate oxidize secondary alcohols more efficiently than its FeIV(O) analog. This trend was reversed for the oxidation of activated primary alcohols where reactions involving FeIV(O) afforded much higher TON's. This reactivity trend can be explained from the differences in bond dissociation energy (BDE) of their corresponding one electron reduced species ([FeIV-OH], ～99 kcal/mol; [FeIII-OH], ～83 kcal/mol) as well as their relative stabilities in the solvent during reaction. This catalytic system was found to be unsuitable for nonconjugated primary alcohol due to the formation of the inactive FeIV(OMe) intermediate after one catalytic cycle.
Copper nanoparticles on hydrotalcite as a heterogeneous catalyst for oxidant-free dehydrogenation of alcohols
Mitsudome, Takato,Mikami, Yusuke,Ebata, Kaori,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information; experimental part, p. 4804 - 4806 (2009/03/12)
We have developed a highly efficient heterogeneous catalytic system using hydrotalcite-supported Cu nanoparticles (Cu/HT) that can successfully promote the oxidant-free dehydrogenation of various alcohols under liquid-phase conditions. The Royal Society of Chemistry.
Oppenauer oxidation of secondary alcohols with 1,1,1-trifluoroacetone as hydride acceptor
Mello, Rossella,Martinez-Ferrer, Jaime,Asensio, Gregorio,Gonzalez-Nunez, Maria Elena
, p. 9376 - 9378 (2008/03/13)
(Chemical Equation Presented) 1,1,1-Trifluoroacetone (2a) reacts as a hydride-acceptor in the Oppenauer oxidation of secondary alcohols (1) in the presence of diethylethoxyaluminum. The oxidant allows for selective oxidation of secondary alcohols in the presence of primary alcohols.
Partial ring hydrogenation of naphthols over supported metal catalysts in supercritical carbon dioxide solvent
Mine, Eiichi,Haryu, Eiji,Arai, Kunio,Sato, Takafumi,Sato, Osamu,Sasaki, Akiyoshi,Rode, Chandrashekhar V.,Shirai, Masayuki
, p. 782 - 783 (2007/10/03)
Selective ring hydrogenation of naphthols to tetrahydronaphthols and tetralones proceeded at 323 K over a charcoal supported rhodium catalyst in supercritical carbon dioxide. Copyright
Selective oxidation of alkylarenes in dry media with potassium permanganate supported on montmorillonite K10
Shaabani, Ahmad,Bazgir, Ayoob,Teimouri, Fatemeh,Lee, Donald G
, p. 5165 - 5167 (2007/10/03)
The solvent-free oxidation of alkylarenes with KMnO4 supported on montmorillonite K10 is reported. The beneficial effects of microwave and ultrasound irradiation on the reactions is described.
Zeolite H-ZSM 5 Catalysed Oxidation of Alcohols with Chromium Trioxide. Part 9. General Synthetic Methods
Pitre, Sangeeta V.,Venkat Ram Reddy,Vankar, Yashwant D.
, p. 462 - 463 (2007/10/03)
A variety of alcohols are oxidised to the corresponding carbonyl compounds in excellent yields by chromium trioxide-H-ZSM 5 in dichloromethane at room temperature.
Carbon-carbon bond formation by electrochemical catalysis in conductive microemulsions
Gao, Jianxin,Rusling, James F.,Zhou, De-Ling
, p. 5972 - 5977 (2007/10/03)
Bicontinuous microemulsions made from oil, water, and surfactants were examined as substitutes for organic solvents in carbon-carbon bond-forming reactions. Conjugated additions of primary alkyl iodides 3a-c to 2-cyclohexen-1-one (4) to give 3-alkyl cyclohexanones 5a-c and cyclization of 2-(4-bromobutyl)-2-cyclohexen-1-one (9) to 1-decalone (10) were mediated by the Co(I)L complex vitamin B12s generated at carbon cloth electrodes under mild conditions. Reaction of the Co(I)L nucleophile with the alkyl halides gives a Co-alkyl complex. Cleavage of the Co-alkyl complexes by using an electrode potential of -0.85 V (all vs SCE) and irradiation with visible light, or a potential of -1.45 V in the dark, were compared. Addition of the resulting alkyl radicals to the activated double bonds gave comparable yields of 3-alkylcyclohexanone 5a-c (70-80% using -0.85 V + light) and 1-decalone (90%, both cleavage modes) 10 in microemulsions and in DMF. Microemulsions containing hexadecyltrimethylammonium bromide (CTAB) gave remarkable stereoselectivity for the trans isomer of 10, while homogeneous DMF and a sodium dodecylsulfate (SDS) microemulsion gave little stereoselectivity.
Iodine-induced transannular coupling of 1,6-cyclodecadiyne
Gu, Xinhong,Sponsler, Michael B.
, p. 1571 - 1574 (2007/10/03)
Treatment of 1,6-cyclodecadiyne (1) with one equivalent of iodine in ether leads to regioselective transannular coupling, producing 1,5-diiodo-2,3,4,6,7,8-hexahydronaphthalene (2) in excellent yield. Solvent-incorporation products are observed in addition to 2 when the reaction is done in benzene, chlorobenzene, or methanol. Bromination of 1 gives analogous products, but the reaction is not as clean.
