2094-73-7Relevant articles and documents
An effective formylation of adamantane with CO initiated by the aprotic organic superacid CBr4·2AlBr3 under mild conditions
Akhrem, Irena,Churilova, Irina,Bernadyuk, Stanislav,Vol'pin, Mark
, p. 5775 - 5778 (1996)
The reaction of adamantane with carbon monoxide at -45°/+20°C over 0.5-2 h, catalyzed by the aprotic organic superacid CBr4·2AlBr3, is described. The formylation of adamantane under CO atmosphere at 0/+20°C in the presence of methylcyclopentane as a source of hydride ion affords 1-adamantanecarbaldehyde (1) in yield 70-72% on adamantane for 1 h.
Oxidation of Deactivated Cage Substrates in the System H2SO4–HNO3
Grin?, I. S.,Ivleva, E. A.,Klimochkin, Yu. N.,Uchaev, I. S.
, p. 412 - 421 (2020)
Abstract: The kinetics of oxidation of 16 carboxylic acid esters of the adamantaneseries in the systemH2SO4–HNO3have been studied, and the effective rate constants have been determined. Thereaction is described by the pseudo-first-order kinetic equation. The primarykinetic isotope effect has been estimated at 2.9±0.3. The rate-determining stepof the oxidation process is cleavage of the adamantane C–H bond. The presence ofan ethyl group at the bridgehead position increases the reactivity of adamantanesubstrates toward oxidation, whereas methyl, ethoxycarbonyl, andethoxycarbonylmethyl groups reduce the reactivity.
One-pot dichlorinative deamidation of primary β-ketoamides
Zheng, Congke,Zhang, Xiaohui,Ijaz Hussain, Muhammad,Huang, Mingming,Liu, Qing,Xiong, Yan,Zhu, Xiangming
supporting information, p. 574 - 577 (2017/01/16)
An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.
Reactions of O-quinone methides with pyridinium methylides: A diastereoselective synthesis of 1,2-dihydronaphtho[2,1- b ]furans and 2,3-dihydrobenzofurans
Osyanin, Vitaly A.,Osipov, Dmitry V.,Klimochkin, Yuri N.
, p. 5505 - 5520 (2013/07/25)
A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.
