220271-74-9Relevant academic research and scientific papers
Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters
Liao, Li-Li,Wang, Zhe-Hao,Cao, Ke-Gong,Sun, Guo-Quan,Zhang, Wei,Ran, Chuan-Kun,Li, Yiwen,Chen, Li,Cao, Guang-Mei,Yu, Da-Gang
, p. 2062 - 2068 (2022/02/10)
Diacids are important monomers in the polymer industry to construct valuable materials. Dicarboxylation of unsaturated bonds, such as alkenes and alkynes, with CO2 has been demonstrated as a promising synthetic method. However, dicarboxylation of C-C single bonds with CO2 has rarely been investigated. Herein we report a novel electrochemical ring-opening dicarboxylation of C-C single bonds in strained rings with CO2. Structurally diverse glutaric acid and adipic acid derivatives were synthesized from substituted cyclopropanes and cyclobutanes in moderate to high yields. In contrast to oxidative ring openings, this is also the first realization of an electroreductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggested that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of the products. Furthermore, we conducted polymerization of the corresponding diesters with diols to obtain a potential UV-shielding material with a self-healing function and a fluorine-containing polyester, whose performance tests showed promising applications.
PSEUDO TR?GER'S BASE AMINES AND MICROPOROUS POLYMERS DERIVED FROM PSEUDO TR?GER'S BASE AMINES
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, (2019/02/02)
Embodiments of the present disclosure describe carbocyclic pseudo Tr?ger's base (CTB) amines. Embodiments of the present disclosure further describe microporous polymers derived from pseudo CTB amines, including, but not limited to, polyimides, CTB ladder
Synthesis and characterization of a microporous 6FDA-polyimide made from a novel carbocyclic pseudo Tr?ger's base diamine: Effect of bicyclic bridge on gas transport properties
Abdulhamid, Mahmoud A.,Ma, Xiaohua,Miao, Xiaohe,Pinnau, Ingo
, p. 182 - 190 (2017/10/17)
A newly designed carbocyclic pseudo Tr?ger's base diamine (CTB) monomer, 2,8-dimethyl-3,9-diamino-5,6,11,12-tetrahydro-5,11-methanodibenzo[a,e][8]annulene (CTBDA) and its isomeric analogue 2,8-dimethyl-(1,7)(4,10)(3,9)-diamino-5,6,11,12-tetrahydro-5,11-me
Synthesis of Functionalized Chiral Carbocyclic Cleft Molecules Complementary to Troeger's Base Derivatives
Kimber, Marc C.,Try, Andrew C.,Painter, Leoni,Harding, Margaret M.,Turner, Peter
, p. 3042 - 3046 (2007/10/03)
The synthesis of optically pure functionalized cleft molecules derived from dibenzobicyclo[b,f][3.3.1]-nona-5a,6a-diene-6,12-dione is reported. These clefts are reminiscent of Troeger's base but contain clefts with different dimensions and additional carbonyl (or alcohol) groups that may be utilized in molecular recognition studies. The 2,8-dimethyl and 2,8-dibromo derivatives were synthesized via an intramolecular Friedel-Crafts acylation and were resolved by chiral HPLC. The 2,8-dinitro derivative was prepared by regiospecific nitration of dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione. The dibromo and dinitro derivatives allow direct access to a range of functionalized molecular clefts. Palladium-catalyzed coupling of the dibromo derivative afforded the disubstituted phenyl, anisole, and acetylene derivatives, while reduction of the dinitro derivative and acetylation provided amino-dione and amide-hydroxyl derivatives. X-ray crystal structures of the dimethyl 12, dibromo 13, di(p-methoxyphenyl) 16, dinitro 18, and dimethyl dinitro 22 derivatives show cleft angles between the planes between the aromatic rings of 84-104°. The synthetic route, structural features, and potential for molecular recognition studies of this class of clefts are compared with those of the more widely studied Troeger's base cleft molecules.
Rigid chiral carbocyclic clefts as building blocks for the construction of new supramolecular hosts
Try, Andrew C.,Painter, Leoni,Harding, Margaret M.
, p. 9809 - 9812 (2007/10/03)
The synthesis and resolution of two chiral carbocyclic cleft molecules containing carbonyl groups on the periphery of the cavity are reported. These compounds are reminiscent of Troger's base but contain a smaller cleft and additional carbonyl (or alcohol
