62133-11-3Relevant academic research and scientific papers
Alkylation of aromatic compounds with adamantan-1-ol
Stepakov,Molchanov,Kostikov
, p. 538 - 543 (2007)
Reactions of substituted benzenes, naphthalenes, and 2- and 3-phenyl-1-benzofurans with adamantan-1-ol in trifluoroacetic acid lead to the formation of the corresponding mono-and diadamantylsubstituted aromatic compounds. Nauka/Interperiodica 2007.
Flow Friedel–Crafts alkylation of 1-adamantanol with arenes using HO-SAS as an immobilized acid catalyst
Kasakado, Takayoshi,Hyodo, Mamoru,Furuta, Akihiro,Kamardine, Aina,Ryu, Ilhyong,Fukuyama, Takahide
, p. 2253 - 2257 (2020/12/15)
In this communication flow Friedel–Crafts alkylation was studied using hydroxy-substituted sulfonic acid-functionalized silica as a catalyst and 1-adamantanol as a model substrate. The reaction of 1-adamantanol (1a) with toluene (2a) proceeded well with 5 min of residence time at 120°C to give good yield of 1-tolyladamantane (3a) as a 1:9 mixture of meta and para isomers. When the flow synthesis was carried out over 2.5 hr of running time, the collected five fractions contain the product 3a in 97–92% yields, suggesting the durability of the catalyst.
Alkylation of aromatic compounds with 1-bromoadamantane in the presence of metal complex catalysts
Khusnutdinov,Shchadneva,Khisamova
, p. 1545 - 1550 (2015/12/30)
Synthesis of aryladamantanes was performed by reaction of 1-bromoadamantane with aromatic compounds in the presence of metal complex catalysts containing Mo, Cr, W, Cu, and Co.
The role of enthalpic and entropic factors in the isomerization equilibrium of aryladamantanes
Pimerzin,Sarkisova
, p. 94 - 102 (2007/10/03)
The chemical equilibrium of five positional isomerization reactions of aryladamantanes with different structures was studied in the liquid phase in the presence of AlCl3 in the range 303-423 K. Contributions to the equilibrium constants were analyzed using experimental and calculated data. The contributions were from symmetry, intermolecular interactions, differences in heat capacities of isomers, overall rotation of molecules, free or hindered rotation of groups in molecules, contribution of vibrations, differences in conformational composition, and intramolecular effects of interaction of substituents in molecules involved in the reaction. The significance of these contributions to the equilibrium constants of the transformations in question was shown. The enthalpies and changes in entropy for the reactions in the liquid and gaseous states were determined and discussed. A comparative analysis of the thermodynamic characteristics of positional isomerization of aryladamantanes, methyladamantanes, methyldiamantanes, and phenylcyclohexanes is given.
Synthesis of Adamantyl-substituted benzenedicarboxylic acids and their derivatives
Betnev,Obukhova,Betnev,Klyuev,Pronin
, p. 399 - 401 (2007/10/03)
A new procedure was developed for the synthesis of adamantyl benzene derivatives by alkylation of o-and m-xylenes with l-adamantyl bromide. Adamantyl-substituted benzenedicarboxylic acids were synthesized by catalytic liquid-phase oxidation of the corresp
Palladium-Catalyzed Coupling Reactions of 1-Bromoadamantane with Styrenes and Arenes
Braese, Stefan,Waegell, Bernard,Meijere, Armin de
, p. 148 - 152 (2007/10/03)
The palladium-catalyzed reaction of 1-bromoadamantane (1-Br) with styrene and donor-substituted styrenes gave the corresponding Heck-type coupling products 3a and b, and 5a and b in moderate yields (15-41percent), while the reaction of 1-Br with various arenes 6a-p under palladium catalysis gave the corresponding adamantyl-substituted arenes 7a-p in good to excellent yields (35-98percent). - Keywords: cross-coupling reactions; metal-catalyzed/adamantylation of styrene and alkenes/arylation of 1-bromoadamantane/Heck reaction; palladium catalysis
Direct Clay-Catalyzed Friedel-Crafts Arylation and Chlorination of the Hydrocarbon Adamantane
Chalais, Stephane,Cornelis, Andre,Gerstmans, Andre,Kolodziejski, Waclaw,Laszlo, Pierre,et al.
, p. 1196 - 1203 (2007/10/02)
Multiple chlorinations and arylations at the tertiary positions of adamantane are promoted by FeCl3-doped K10 montmorillonite in CCl4 or in aromatic solvents.The process, remarkably easy implement, can be tailored to selective formation of monosubstituted 1-adamantyl derivatives or 1,3-disubstituted adamantanes.The process achieves alkylation at the meta- and para-positions of toluene leading to a purely statistical distribution and displays no substrate specificity in competition experiments between toluene and benzene.
REACTIONS OF ADAMANTYL NITRATES WITH AROMATIC COMPOUNDS.
Moiseev, I. K.,Doroshenko, R. I.
, p. 1067 - 1069 (2007/10/02)
It has been shown to be possible to use adamantyl nitrates in the synthesis of mono- and diaryladamantanes.The effects of substituents and the acidity of the medium on the yields of reaction products have been studied.
