- Improved approach towards synthesis of adamantane-1,3,5-triol
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1-Adamantanol can be converted into adamantane-1,3,5-triol in the presence of N-hydroxylphthtalimide, cobalt(II) acetylacetonate, and manganese dioxide under oxygen atmosphere in glacial acetic acid.
- Ivleva,Platonov,Klimochkin
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p. 1830 - 1833
(2015/10/12)
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- Synthesis of adamantane-based trimeric cationic surfactants
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Three trimeric quaternary ammonium surfactants, having adamantane cores and different carbon chains, were synthesized using adamantane as the starting raw material. The target compounds were confirmed by elemental analysis, 1H NMR, 13C NMR, and mass spectroscopy. The influences of reaction conditions on the yields of the key intermediate product 1,3,5-trihydroxyadamantane (3) were investigated. Surface properties of the target compounds were measured. The critical micelle concentration values of 1a, 1b, and 1c were 2mM, 1mM, and 0.5mM, respectively.
- Zhu, Hua,Guo, Jianwei,Yang, Chufen,Liu, Sa,Cui, Yingde,Zhong, Xing
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p. 1161 - 1167
(2013/03/29)
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- Electronic tuning of iron-oxo-mediated C-H activation: Effect of electron-donating ligand on selectivity
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We have reported previously that an iron(III) complex supported by an anionic pentadentate monoamido ligand, dpaqH (dpaq H=2-[bis(pyridin-2-ylmethyl)]amino-N-quinolin-8-yl-acetamido), promotes selective C-H hydroxylation with H2O2 with high regioselectivity. Herein, we report on the preparation of FeIII-dpaq derivatives that have a series of substituent groups at the 5-position of a quinoline moiety in the parent ligand dpaqH (dpaqR, R: OMe, H, Cl, and NO2), and examine them with respect to their catalytic activity in C-H hydroxylation with H2O2. As the substituent group becomes more electron-withdrawing, both the selectivity and the turnover number increase, but the selectivity of epoxidation shows the opposite trend. Copyright
- Hitomi, Yutaka,Arakawa, Kengo,Kodera, Masahito
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supporting information
p. 14697 - 14701
(2013/11/06)
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- Production of adamantanediols
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Adamantanediols are produced by the hydroxylation of adamantane compounds in a water/organic solvent two-phase system in the presence of a ruthenium compound and a hypochlorite. Throughout the hydroxylation, the hypochlorite concentration in the water phase is regulated within a narrow limited range, for example, by monitoring the pH of the reaction system. With such a control of the hypochlorite concentration, the adamantanediols are produced in a high selectivity and a high yield.
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Page column 5-7
(2008/06/13)
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- Production of adamantanediols
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Adamantanediols are produced by the hydroxylation of adamantane compounds in a water/organic solvent two-phase system in the presence of a ruthenium compound and a hypochlorite. Throughout the hydroxylation, the hypochlorite concentration in the water phase is regulated within a narrow limited range, for example, by monitoring the pH of the reaction system. With such a control of the hypochlorite concentration, the adamantanediols are produced in a high selectivity and a high yield.
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- Oxidations by methyl(trifluoromethyl) dioxirane. 3. Selective polyoxyfunctionalization of adamantane
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Adamantane (1) can be converted directly into adamantan-1,3,5-triol (5) and into adamantan-1,3,5,7-tetraol (6) under remarkably mild conditions by employing an excess of isolated methyl (trifluoromethyl)dioxirane (3a) in solution. This new dioxirane species was found to be over 7,000-fold more reactive than dimethyldioxirane (3b) in performing adamantane hydroxylations.
- Mello, Rossella,Cassidei, Luigi,Fiorentino, Michele,Fusco, Caterina,Curci, Ruggero
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p. 3067 - 3070
(2007/10/02)
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