- Hydroxylation of Acetoxy-p-menthenes in the Cultured Cells of Nicotiana tabacum. Epoxidation of the Carbon-Carbon Double Bond
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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.
- Hirata, Toshifumi,Izumi, Shunsuke,Ekida, Teiji,Suga, Takayuki
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- Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes
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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.
- Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido
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supporting information
p. 8313 - 8320
(2021/03/08)
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- 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)
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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.
- De Vekki,Uvarov,Bel'skii,Skvortsov
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p. 1288 - 1294
(2008/02/03)
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- The Diepoxides of Terpinolene
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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.
- Carman, Raymond M.,Rayner, Anthony C.
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p. 195 - 202
(2007/10/02)
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- Chemistry Around δ-Terpineol
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Bromination, hydroboration, epoxidation, 1,2-dihydroxylation and acidification reactions upon δ-terpineol are described.
- Bull, Steven D.,Carman, Raymond M.
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p. 1869 - 1880
(2007/10/02)
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- 7-Hydroxy-1,8-cineole and 7-Cineolic Acid. Two New Possum Urinary Metabolites
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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.
- Bull, Steven D.,Carman, Raymond M.,Carrick, Frank N.,Klika, Karel D.
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p. 441 - 447
(2007/10/02)
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