- Modified Marko's aerobic oxidation of alcohols under atmospheric pressure with air or molecular oxygen at room temperature
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A modified version of Marko's aerobic oxidation procedure, using highly pure (99.995+%) CuCl with 4,7-diphenyl-1,10-phenanthroline (dpPhen), DBAD, and Cs2CO3 (98% purity) successfully oxidized primary and secondary alcohols to the corresponding aldehydes and ketones in excellent yield at room temperature with either air or molecular oxygen under atmospheric pressure.
- Nishii, Takeshi,Ouchi, Tomomi,Matsuda, Aya,Matsubara, Yuka,Haraguchi, Yuuko,Kawano, Tomomi,Kaku, Hiroto,Horikawa, Mitsuyo,Tsunoda, Tetsuto
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p. 5880 - 5882,3
(2020/07/31)
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- The oxidation of alcohols in N-oxyl-immobilized silica gel/aqueous NaOCl disperse systems. A prominent access to a column-flow system
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The oxidation of alcohols was performed successfully in a disperse system with N-oxyl-adsorbed or immobilized silica gel as a disperse phase and aqueous NaOCl as a disperse medium. In the disperse system, the oxidation of sec-alcohols afforded the corresponding ketones, while prim-alcohols were oxidized to aldehydes and/or carboxylic acids depending on their structures and reaction conditions. The N-oxyl-immobilized silica gel was recovered and repeatedly used without a significant change in the product yields. A column-flow system was also investigated for the oxidation of alcohols by use of a newly devised column packed with the N-oxyl-immobilized silica gel.
- Tanaka, Hideo,Chou, Jingyu,Mine, Machiko,Kuroboshi, Manabu
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p. 1745 - 1755
(2007/10/03)
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- Oxidation of Diols and Ethers by NaBrO3/NaHSO3 Reagent
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NaBrO3 combined with NaHSO3 was found to be an excellent oxidizing reagent of alcohols, diols, and ethers under mild conditions. A variety of aliphatic and cyclic diols were selectively oxidized with satisfactory yields to the corresponding hydroxy ketones and/or diketones, which are difficult to selectively prepare due to a concomitant formation of cleaved products. For example, 2-hydroxycyclohexanone and 1,2-cyclohexanedione were selectively formed by allowing 1,2-cyclohexanediol to react with NaBrO3/NaHSO3 reagent in a selected solvent. On the other hand, an alkyl ether, such as dioctyl ether, reacted with NaBrO3/NaHSO3, in water at room temperature to give octyl octanoate in 82% yield. The same oxidation at higher temperature (60°C) produced the α-brominated ester, octyl 2-bromooctanoate, which is considered to be formed through an alkenyl alkyl ether as the intermediate. The treatment of 1-ethoxy-l-heptene with NaBrO3/NaHSO3 afforded ethyl 2-bromoheptanoate and 2-bromoheptanoic acid as the major products.
- Sakaguchi, Satoshi,Kikuchi, Daisuke,Ishii, Yasutaka
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p. 2561 - 2566
(2007/10/03)
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- A Selective and Efficient Method for Alcohol Oxidations Mediated by N-Oxoammonium Salts in Combination with Sodium Bromite
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The oxidation of primary and secondary alcohols leading to aldehydes, carboxylic acids, and ketones has been carried out in a N-oxoammonium salts-NaBrO2 system.Sodium bromite as a stoichiometric oxidizing reagent activates N-oxyl compounds (recycling catalysts) to their N-oxoammonium salts in a weakly basic medium, which oxidize primary hydroxyl groups preferentially rather than secondary ones to the corresponding aldehydes.Calcium hypochlorite is used as an alternative terminal oxidant in the same media.The procedure, applicable to the selective formation of γ- and δ-lactones, β-hydroxy aldehydes, and 2-acetoxy ketones, is advantageous in terms of reagent cost, safety, and ease of operation.
- Inokuchi, Tsutomo,Matsumoto, Sigeaki,Nishiyama, Tokio,Torii, Sigeru
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p. 462 - 466
(2007/10/02)
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