16429-21-3Relevant articles and documents
Lactonization of Hydroxy Ester over Hydrous Zirconium(IV) Oxide Modified by Trimethylsilyl Chloride
Kuno, Hideyuki,Shibagaki, Makoto,Takahashi, Kyoko,Matsushita, Hajime
, p. 1305 - 1307 (1993)
The lactonization of hydroxy esters was performed over hydrous zirconium(IV) oxide modified by trimethylsilyl chloride.In the case of both primary and secondary hydroxy esters, lactones were obtained in high yield.In addition, it was elucidated that modified-hydrous zirconium(IV) oxide is superior to hydrous zirconium(IV) oxide regarding selectivity in lactonization.
9-azanoradamantane N—oxyl compound and method for producing same, and organic oxidation catalyst and method for oxidizing alcohols using 9-azanoradamantane N—oxyl compound
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Page/Page column 35-36, (2015/09/23)
An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.
Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols
Doi, Ryusuke,Shibuya, Masatoshi,Murayama, Tsukasa,Yamamoto, Yoshihiko,Iwabuchi, Yoshiharu
, p. 401 - 413 (2016/10/12)
The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.
Oxidation of the cyclopentanone and cyclohexanone alkyl derivatives in a pseudohomogeneous system without a phase transfer agent
Alimardanov,Garibov,Abbasov,Sadygov,Abdullaeva,Dzhafarova
experimental part, p. 1664 - 1670 (2011/12/02)
The reaction of catalytic oxidation of C5-C12 alkyl- and cycloalkylcyclopentanones and -cyclohexanones to lactones in a pseudohomogeneous system without the participation of phase transfer agents was investigated. It was established that the catalytic systems prepared on the basis of molybdenum and tungsten blue (MeOnBrm, where Me = Mo, W, n = 1, 2, m = 2, 3) and H3PO4 deposited on powdered activated carbon AG-3 at 40-60°C, at 5-6 h duration exhibit a high selectivity in the reaction of nucleophilic addition of oxygen to the ketones with the formation of the valero- and caprolactones. Pleiades Publishing, Ltd., 2011.
Highly efficient synthesis of medium-sized lactones via oxidative lactonization: Concise total synthesis of isolaurepanf
Ebine, Makoto,Suga, Yuto,Fuwa, Haruhiko,Sasaki, Makoto
scheme or table, p. 39 - 42 (2010/04/26)
A catalytic amount of TEMPO in the presence of PhI(OAc)2 effected oxidative lactonization of 1,6- and 1,7-diols, directly affording seven- and eight-membered lactones, respectively, in good yields. The Royal Society of Chemistry 2010.
Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones
Abbasov,Alimardanov,Suleimanova
, p. 621 - 626 (2007/10/03)
Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.
Lipase-catalysed Baeyer-Villiger Reactions
Lemoult, Stephanie C.,Richardson, Paul F.,Roberts, Stanley M.
, p. 89 - 92 (2007/10/02)
The Baeyer-Villiger Oxidation of some 2- and 3-substituted cyclopentanones and cyclohexanones using myristic acid and hydrogen peroxide is catalysed by Candida anatarctica lipase.
Synthesis of Medium Ring Ethers. Part 2. Synthesis of the Fully Saturated Carbon Skeleton of Laurencia Non-terpenoid Ether Metabolites Containing Seven-, Eight- and Nine-membered Rings
Carling, Robert W.,Clark, J. Stephen,Holmes, Andrew B.
, p. 83 - 94 (2007/10/02)
A general method for the construction of medium ring ethers is described in which a 2-substituted cycloalkanone was subjected to a Baeyer-Villiger ring expansion to the lactone, Tebbe methylenation of which afforded the enol ether which was subjected to a hydroboration-oxidation sequence to afford the 2,n-disubstituted oxacycle (n = ring size).Application of this procedure has led to efficient syntheses of the fully saturated skeletons corresponding to the naturally occurring Laurencia metabolites containing 2,n-dialkyl substituted seven- (isolaurepan), eight- (lauthisan and laurenan) and nine-membered (obtusan) ethers.
