5001-18-3Relevant articles and documents
Synthesis of adamantane-based trimeric cationic surfactants
Zhu, Hua,Guo, Jianwei,Yang, Chufen,Liu, Sa,Cui, Yingde,Zhong, Xing
, p. 1161 - 1167 (2013)
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.
Photoassisted oxygenation of alkane catalyzed by ruthenium complexes using 2,6-dichloropyridine N-oxide under visible light irradiation
Yamaguchi, Motowo,Kumano, Takashi,Masui, Dai,Yamagishi, Takamichi
, p. 798 - 799 (2004)
The chloro(Me2SO)ruthenium(II) complexes with tris(2-pyridylmethyl)amine or its derivative catalyses the selective, stereospecific, and photoregulative alkane oxidation in the presence of 2,6-dichloropyridine N-oxide under visible light irradiation.
Selective biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora (I.M.I. 342950)
Bailey, Patrick D.,Higgins, Stanley D.,Ridyard, Colin H.,Roberts, Stanley M.,Rosair, Georgina M.,Whittaker, Roger A.,Willetts, Andrew J.
, p. 1833 - 1834 (1996)
The biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora in a whole-cell oxidation system exclusively generated 3-hydroxy and 4ax-hydroxy derivatives; the assignments were confirmed by three X-ray crystal structure determinations.
Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with transition metal salts
Ishii, Yasutaka,Kato, Susumu,Iwahama, Takahiro,Sakaguchi, Satoshi
, p. 4993 - 4996 (1996)
Adamantanes were successfully converted into the corresponding mono- and dihydroxy adamantanes with molecular oxygen in the presence of N- hydroxyphthalimide (NHPI) combined with cobalt salts under mild conditions. For example, exposure of adamantane under oxygen atmosphere in the presence of NHPI (10 mol%) and Co(acac)2 (0.5 mol%) in acetic acid at 75 °C for 6 h afforded adamantan-1-ol (43 %) and adamantane-1,3-diol (40 %) along with adamantan-2-one (8 %) in 93 % conversion. Similarly, 1,3-dimethyladamantane produced 3,5-dimethyladamantan-1-ol (47 %) and 5,7-dimethyladamantane-1,3- diol (37 %).
Ruthenium-Immobilized Periodic Mesoporous Organosilica: Synthesis, Characterization, and Catalytic Application for Selective Oxidation of Alkanes
Ishito, Nobuhiro,Kobayashi, Hirokazu,Nakajima, Kiyotaka,Maegawa, Yoshifumi,Inagaki, Shinji,Hara, Kenji,Fukuoka, Atsushi
, p. 15564 - 15569 (2015)
Periodic mesoporous organosilica (PMO) is a unique material that has a crystal-like wall structure with coordination sites for metal complexes. A Ru complex, [RuCl2(CO)3]2, is successfully immobilized onto 2,2'-bipyridine (BPy) units of PMO to form a single-site catalyst, which has been confirmed by various physicochemical analyses. Using NaClO as an oxidant, the Ru-immobilized PMO oxidizes the tertiary C-H bonds of adamantane to the corresponding alcohols at 57 times faster than the secondary C-H bonds, thereby exhibiting remarkably high regioselectivity. Moreover, the catalyst converts cis-decalin to cis-9-decalol in a 63% yield with complete retention of the substrate stereochemistry. The Ru catalyst can be separated by simple filtration and reused without loss of the original activity and selectivity for the oxidation reactions.
Method for preparing 1,3-adamantane diol by taking 1-bromo-adamantane as initial raw material
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Paragraph 0037; 0041-0045; 0049-0053; 0057-0061; 0065-0069;, (2021/01/25)
The invention discloses a method for preparing 1,3-adamantane diol by taking 1-bromo-adamantane as an initial raw material, which comprises the following steps: (1) dissolving 1-bromo-adamantane in anorganic solvent, and adding concentrated sulfuric acid and nitric acid to carry out nitration reaction, thereby obtaining an organic solution phase; and (2) mixing the obtained organic solution phasewith a water solution of a strong base, and carrying out a hydrolysis reaction to obtain the product. According to the method, the 1,3-adamantane diol is synthesized by taking 1-bromo-adamantane which is easily available and low in cost as an initial raw material, so that the defects of high production cost and complex separation and purification of a target product in an existing industrial production process taking the 1,3-dibromo adamantane as a raw material are overcome; particularly, the mixed acid phase and the alkaline water liquid phase can be recycled and adjusted for multiple times,so that the environment-friendly treatment cost of the production waste is greatly reduced.
Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds
Doiuchi, Daiki,Uchida, Tatsuya
, p. 7301 - 7305 (2021/10/01)
We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)2 and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation. Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C-H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as d-[3-17O/18O]-mannose can be prepared in a multigram scale.
