89923-77-3Relevant articles and documents
Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes
Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 8313 - 8320 (2021/03/08)
Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.
Method for preparing limonene from 3-carene
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Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023-0025, (2017/04/27)
The invention discloses a method for preparing limonene from 3-carene. The method comprises the following steps: (1) preparing terpin from 3-carene in the presence of sulfuric acid, wherein the reaction temperature is kept at 15-35 DEG C; and (2) preparing limonene from the terpin in the presence of sulfuric acid, wherein the reaction temperature is kept at 0-10 DEG C. The invention aims at providing a method for preparing limonene from 3-carene, wherein in the method, limonene is prepared from cheap 3-carene, the conversion rate is high while the preparation flow is relatively simple, and the prepared limonene is separated from other byproducts relatively easily.
Addition of perfluoroalkanoic acids to (R)-(+)-limonene
Trishin,Shafeeva,Tamm
, p. 545 - 550 (2013/06/27)
Perfluoroalkanoic acids with different lengths of the perfluoroalkyl radical selectively add under mild conditions to the exocyclic double C=C of limonene to give the corresponding Markovnikov adducts, α-terpinyl perfluoroalkanoates. The reaction in the p
Hydration of α-pinene in a triphasic system consisting of α-pinene, water, and Cs2.5H0.5PW12O 40-SiO2 composite
Horita, Naoto,Kamiya, Yuichi,Okuhara, Toshio
, p. 1346 - 1347 (2007/10/03)
Cs2.5H0.5PW12O40-SiO 2 composite combined with (3-aminopropyl)triethoxysilane exhibited greater activity and selectivity for hydration of α-pinene at 333 K in a triphasic system (α-pinene/water/solid acid) compared to previously reported water-tolerant catalysts such as zeolites, polymer-resins (Amberlyst 15 and Nafion-H), oxides, and liquid acids such as H3PW 12O40 and H2SO4. The selectivity toward alcohols, including mono- and dialcohols, was approximately 80% over Cs2.5H0.5PW12O40-SiO2 composite. Copyright
Reaction of platinum complexes with (+)-α-pinene and (+)-limonene. Synthesis, molecular structure, and catalytic activity of dichloro(η 4-[p-mentha-1,8{9}-diene])platinum(II)
De Vekki,Uvarov,Bel'skii,Skvortsov
, p. 1288 - 1294 (2008/02/03)
The transformations of platinum(II) and platinum(IV) complexes with inner-and outer-sphere ligands by the action of (+)-α-pinene and (+)-limonene were studied. Reduction of the metal complex is the main process whose rate increases in the following outer-sphere ligand series: (Me 2SO)2H+ 3NH+ - +. The reaction of K2PtCl4 with α-pinene gave cis-terpine monohydrate and dichloro-η4- [p-mentha-1,8(9)-diene]platinum(II), and their structure was proved by X-ray analysis. The complex belongs to monoclinic crystal system, the Pt-Cl and Pt-C bonds therein have different lengths, the ClPtCl angle is 85.88°, and the C=C bond plane is orthogonal to the square coordination core. Dichloro-η4-[p-mentha-1,8(9)-diene]-platinum(II) was tested as catalyst in the hydrosilylation of acetophenone with diphenylsilane. Nauka/Interperiodica 2006.
The Diepoxides of Terpinolene
Carman, Raymond M.,Rayner, Anthony C.
, p. 195 - 202 (2007/10/02)
The structures of the racemic 1,2:4,8-diepoxy-p-menthanes, the diepoxides of terpinolene, are revised.The major isomer has the trans relationship between the two epoxides.
7-Hydroxy-1,8-cineole and 7-Cineolic Acid. Two New Possum Urinary Metabolites
Bull, Steven D.,Carman, Raymond M.,Carrick, Frank N.,Klika, Karel D.
, p. 441 - 447 (2007/10/02)
7-Hydroxy-1,8-cineole (3a) and the corresponding carboxylic acid (3b) have been isolated from the urine of brushtail possums (Trichosurus vulpecula: Marsupialia) fed a diet enhanced with 1,8-cineole.Chemical syntheses of these two novel metabolites are described.
Chemistry Around δ-Terpineol
Bull, Steven D.,Carman, Raymond M.
, p. 1869 - 1880 (2007/10/02)
Bromination, hydroboration, epoxidation, 1,2-dihydroxylation and acidification reactions upon δ-terpineol are described.
Ultrasound in Organic Synthesis. 18. Selective Oxymercuration via Sonochemically in Situ Generated Mercury Salts
Einhorn, J.,Einhorn, C.,Luche, J. L.
, p. 4479 - 4481 (2007/10/02)
Selective mercuration of diolefins is favored by a proper choice of the mercuric salt, which can be generated in situ from mercuric oxide and the corresponding acid under sonochemical activation.
Hydroxylation of Acetoxy-p-menthenes in the Cultured Cells of Nicotiana tabacum. Epoxidation of the Carbon-Carbon Double Bond
Hirata, Toshifumi,Izumi, Shunsuke,Ekida, Teiji,Suga, Takayuki
, p. 289 - 294 (2007/10/02)
The process of the formation of glycols in the biotransformation of 1-acetoxy-p-menth-4(8)-ene and 8-acetoxy-p-menth-1-ene in the cultured cells of Nicotiana tabacum was examined.The formation of the glycols was found to result from epoxidation of the C-C double bond, followed by hydrolysis of the resulting epoxides.
