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Janus-type BN-embedded perylene diimides via a“shuffling”strategy:Regioselective functionalizable building block towards high-performance n-type organic semiconductors
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作者 Kexiang Zhao Zongrui Wang +4 位作者 Qi-Yuan Wan Jing-Cai Zeng Li Ding Jie-Yu Wang Jian Pei 《Chinese Chemical Letters》 2025年第6期417-422,共6页
Regioselevtive functionalization of perylene diimides(PDIs)at bay area often requires multistep synthesis and strenuous recrystallization.Direct bromination of perylene diimides only afford the 1,6 and 1,7-regioisomer... Regioselevtive functionalization of perylene diimides(PDIs)at bay area often requires multistep synthesis and strenuous recrystallization.Direct bromination of perylene diimides only afford the 1,6 and 1,7-regioisomers.More importantly,the 1,6-dibromo regioisomers could only be separated by preparative HPLC.Herein,we report a promising strategy for constructing Janus backbone of BN-doped perylene diimide derivatives.This Janus-type configuration results in the unique regioselective functionalization of BN-JPDIs,which yields exclusively the 1,6-regioisomers.Further investigation shows that the Janus-type configuration leads to a net dipole moment of 1.94 D and intramolecular charge transfer,which causes substantial changes on the optoelectronic properties.Moreover,the single crystal organic field-effect transistors based on BN-JPDIs exhibit electron mobilities up to 0.57 cm^(2)V^(-1)s^(-1),showcasing their potential as versatile building block towards high-performance n-type organic semiconductors. 展开更多
关键词 BN heterocycles Perylene diimides regioselective functionalization Intramolecular charge transfer N-type organic semiconductors
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Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes
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作者 Wujun Jian Mong-Feng Chiou +2 位作者 Yajun Li Hongli Bao Song Yang 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第5期141-144,共4页
Borylation of 1,3-enynes with bis(boronate)compounds often ends up with the formation of hydroborylated products,leaving the diborylation of 1,3-enynes for the formation of 1,4-diborylated allenes to be challenging.He... Borylation of 1,3-enynes with bis(boronate)compounds often ends up with the formation of hydroborylated products,leaving the diborylation of 1,3-enynes for the formation of 1,4-diborylated allenes to be challenging.Herein,a copper-catalyzed chemo-,regio-,and stereo-selective diborylation of 1,3-enynes for the efficient construction of 1,4-diborylated allenes under base-free conditions was reported.A wide range of 1,3-enynes bearing various functional groups can participant in the reaction and afforded the corresponding 1,4-diborylated allenes in good to excellent yields,which was enabled by the protocol of Bpin to BF3K conversion.the borylcopper species was supposed to selectively attack the C-C triple bond of the 1,3-enynes. 展开更多
关键词 Copper catalysis regioselective 1 3-Enynes BORYLATION ALLENES
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Regioselective oxidation of tetracycline by permanganate through alternating susceptible moiety and increasing electron donating ability 被引量:3
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作者 Xiaohua Jiang William AJefferson +6 位作者 Dean Song Hanyang Cheng Fengmin Li Zhimin Qiang Aiqian Zhang Huijuan Liu Jiuhui Qu 《Journal of Environmental Sciences》 SCIE EI CAS CSCD 2020年第1期281-288,共8页
Permanganate has attracted much attention in wide range of chemistry and particularly in degradation of environmental pollutants.However,few studies have discussed the feature of regioselective reactivity of permangan... Permanganate has attracted much attention in wide range of chemistry and particularly in degradation of environmental pollutants.However,few studies have discussed the feature of regioselective reactivity of permanganate with specific moiety of the target compound.Herein,we studied the reaction between permanganate and tetracycline that is an emerging micropollutant with different species containing several electron-rich groups.The second-order rate constants increased from 6.0 to 9.0 and could be quantitatively modeled by considering the speciation of both reactants,yielding kTC0=11.7(mol/L)^-1 sec^-1,kTC-=35.7(mol/L)^-1 sec^-1,kTC2-=43.1(mol/L)^-1 sec^-1 for individual reaction channels.Degradation products were then identified as the hydroxylated and demethylated compounds.The result suggested a rate-limiting step of simple hydroxylation at the phenolic and/or alkene moieties,while the demethylation should be caused by the unavoidably formed manganese oxide via single electron oxidation.This is supported by the DFT calculation,indicating the primary oxidation of phenolic group of TC0 with activation barrier of 44.5 kcal/mol and of alkene group of TC-and TC2-with activation barriers of 44.0 and 43.4 kcal/mol,respectively.This is in agreement with the experimental results,implying the alternation of regioselectivity associated with the deprotonation process.The result was further supported by performing the Fukui function and electrostatic potential analysis,reflecting the more probable site and better electron donating tendency beneficial to the permanganate oxidation. 展开更多
关键词 Permanganate oxidation of tetracycline regioselective reactivity Rate-limiting hydroxylation step Altered susceptible moiety Increased electronegativity
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[Bmim]Br_3 as a New Reagent for Regioselective Mono-bromination of Activated Aromatics under Solvent-free Conditions 被引量:2
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作者 Zhang Gao LE Zhen Chu CHEN +1 位作者 Yi HU Qin Guo ZHENG 《Chinese Chemical Letters》 SCIE CAS CSCD 2005年第8期1007-1009,共3页
Reaction of activated aromatics containing phenobs, naphthol, methoxynaphthalenes,anisole etc. with 1-butyl-3-methylimidazolium tribromide ([Bmim]Br3) under solvent-free conditions, selectively gave the correspondin... Reaction of activated aromatics containing phenobs, naphthol, methoxynaphthalenes,anisole etc. with 1-butyl-3-methylimidazolium tribromide ([Bmim]Br3) under solvent-free conditions, selectively gave the corresponding monobromination products with excellent yields. 展开更多
关键词 Activated aromatics regioselective [Bmim]Br3.
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Synthetic studies on the construction of 7-O-methylquercetin through regioselective protection and alkylation of quercetin 被引量:1
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作者 Nian Guang LI Zhi Hao Shi +6 位作者 Yu Ping Tang Jian Ping Yang Tu Lin Lu Feng Zhang Yi Wen Huang Zhen Jiang Wang Jin Ao Duan 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第1期5-8,共4页
Synthetic studies on the construction of 7-O-methylquercetin from quercetin in 36% yield in four steps is reported, this strategy relies on one hand on the selective protection of the catechol group with dichlorodiphe... Synthetic studies on the construction of 7-O-methylquercetin from quercetin in 36% yield in four steps is reported, this strategy relies on one hand on the selective protection of the catechol group with dichlorodiphenylmethane using dephenyl ether as a solvent, on the other hand, on the selective protection of the 3-hydroxyl group with benzyl bromide, these two different protecting groups can be removed under the same hydrogenation. 展开更多
关键词 7-O-Methylquercetin Hemisynthesis regioselective protection ALKYLATION High yield
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An efficient chemo-and regioselective three-component synthesis of pyridazinones and phthalazinones using activated KSF 被引量:1
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作者 L.Zare N.O.Mahmoodi +2 位作者 A.Yahyazadeh M.Mamaghani K.Tabatabaeian 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第5期538-541,共4页
The first three-component and regioselective synthesis of pyridazinones and phthalazinones from arenes,anhydrides and ArNHNH;in the presence of efficient recyclable heterogeneous catalyst,montmorillonite-KSF,in high y... The first three-component and regioselective synthesis of pyridazinones and phthalazinones from arenes,anhydrides and ArNHNH;in the presence of efficient recyclable heterogeneous catalyst,montmorillonite-KSF,in high yield and short reaction time is reported. 展开更多
关键词 regioselective PYRIDAZINONES Phthalazinones Montmorillonite-KSF
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Pseudo four-component and regioselective synthesis of 4-amino-3,5-dicyano-6-arylphthalates using triethylamine catalyst 被引量:2
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作者 Bagher Mohammadi Mansoor Shafieey +1 位作者 Hamed Kazemi Ali Ramazani 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第6期497-499,共3页
An efficient triethylamine-catalyzed synthesis of 4-amino-3,5-dicyano-6-arylphthalates is described.A one-pot,simple pseudo four-component reaction between arylaldehydes,dialkyl acetylenedicarboxylates, and twice as m... An efficient triethylamine-catalyzed synthesis of 4-amino-3,5-dicyano-6-arylphthalates is described.A one-pot,simple pseudo four-component reaction between arylaldehydes,dialkyl acetylenedicarboxylates, and twice as much malononitrile gave 4-amino-3,5-dicyano-6-arylphthalates in good to excellent yields. 展开更多
关键词 Multicomponent reactions Ring closure Triethylamine Catalysis regioselective 4-Amino-3 5-dicyano-6-arylphthalates
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Regioselective Bromination of 3, 4-Dimethoxytoluene with N-Bromosuccinimide 被引量:1
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作者 Hong Min MA Zhan Zhu LIU Shi Zhi CHEN 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第4期371-374,共4页
The selective brominations of 3, 4-dimethoxytoluene with N-bromosuccinimide were reported. The nuclear and side-chain brominated products were obtained under different reaction conditions. The mechanism was also discu... The selective brominations of 3, 4-dimethoxytoluene with N-bromosuccinimide were reported. The nuclear and side-chain brominated products were obtained under different reaction conditions. The mechanism was also discussed. 展开更多
关键词 BROMINATION 3 4-dimethoxy toluene N-bromosucinimide regioselective bromination.
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1-(1-Alkylsulfonic)-3-methylimidazolium chloride as a reusable Brφnsted acid catalyst for the regioselective azidolysis of epoxides under solvent-free conditions 被引量:1
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作者 Sobhan Rezayati Eshagh Rezaee Nezhad Rahimeh Hajinasiri 《Chinese Chemical Letters》 SCIE CAS CSCD 2016年第6期974-978,共5页
In this study, 1-(1-alkylsulfonic)-3-methylimidazolium chloride as a new, green, and reusable Br?nsted acid catalyst was prepared. In this protocol, we used for the regioselective ring-opening reactions of various ... In this study, 1-(1-alkylsulfonic)-3-methylimidazolium chloride as a new, green, and reusable Br?nsted acid catalyst was prepared. In this protocol, we used for the regioselective ring-opening reactions of various epoxiodes with sodium azide to afford the corresponding b-azido alcohols in excellent yields and short reaction time under mild and neutral reaction conditions. This method offers several advantages including excellent regioselectivity, clean reactions, simple work-up procedure, a recyclable catalyst,and use of an eco-friendly catalyst. 展开更多
关键词 Ionic liquids(ILs) β-Azido alcohols Ring opening regioselective Br?nsted acid
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An efficient regioselective sonochemical synthesis of novel 4-aryl-3-methyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-ones 被引量:1
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作者 Abbas Azimi Roshan Manouchehr Mamaghani +1 位作者 Nosrat Ollah Mahmoodi Farhad Shirini 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第4期399-402,共4页
An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-l//-pyrazolo[34-b]pyridin-6(7H)ones via the reaction of 5-amino-3-methyl-1H-pyrazole,Meldrum's acid and various arylalde... An efficient ultrasound-assisted preparation of a series of novel 4-aryl-3-methyl-4,5-dihydro-l//-pyrazolo[34-b]pyridin-6(7H)ones via the reaction of 5-amino-3-methyl-1H-pyrazole,Meldrum's acid and various arylaldehydes using one-pot three-component approach is described.This rapid method produced the products in short reaction times(3-4 min) and excellent yields(87-95%). 展开更多
关键词 Pyrazolo[3 4-b]pyridin-6(7H)-one Meldrum's acid 5-Amino-3-methylpyrazole One-pot Ultrasonic irradiation Three-component regioselective
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Preparation of Cellulose Nanofibrils by Multi-Site Regioselective Oxidation 被引量:1
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作者 Liying Song Xixiang Pei +2 位作者 Rui Li Haitao Chen Xiaozheng Sun 《Journal of Renewable Materials》 SCIE EI 2020年第10期1269-1282,共14页
Cellulose nanofibrils(CNFs)are promising sustainable materials that can be applied to nanocomposites,as well as medical and life-sciences devices.However,methods for the preparation of these important materials are en... Cellulose nanofibrils(CNFs)are promising sustainable materials that can be applied to nanocomposites,as well as medical and life-sciences devices.However,methods for the preparation of these important materials are energy intensive because heating and mechanical disintegration are required to produce cellulose fibers below 100 nm in size.In this study,CNFs were prepared through the multi-site regioselective oxidation of cellulose with 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO)and periodate at room temperature(20–25°C),without any mechanical-disintegration treatment.Transmission electron microscopy(TEM)revealed that the CNFs had the average widths of 14.1,55.4,and 81.9 nm for three different treatments.Fourier-transform infrared spectroscopy revealed that carboxyl groups were created on the surfaces of the microfibrils,while X-ray diffraction studies showed that the cellulose I structure was maintained after oxidation,and that the cellulose nanofibril crystallinity index exceeded 70%.These results demonstrate that CNFs can be prepared by multi-site regioselective oxidation at room temperature in the absence of mechanical disintegration.In addition,a model was developed to calculate the total content of carboxylate and aldehyde groups of CNFs prepared by the TEMPO mediate oxidation,the periodate oxidation,and the multi-site regioselective oxidation methods based on the particle width determined by TEM.The calculated values of the model were in good agreement with the total content(experimental value)of carboxylate and aldehyde groups of CNFs prepared by the TEMPO-mediated oxidation and the multi-site regioselective oxidation methods.However,the model was not valid for CNFs prepared by the periodate oxidation method. 展开更多
关键词 Cellulose nanofibril multi-site regioselective oxidation total content of carboxylate and aldehyde groups particle width
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Synthesis of kanamycin A derivatives by regioselective masking drug resistant enzymes targeting hydroxyl groups
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作者 陈颖 孟祥豹 +2 位作者 陈桂辉 潘攀 李中军 《Journal of Chinese Pharmaceutical Sciences》 CAS 2008年第2期138-143,共6页
The 3'-OH, 4'-OH and 2"-OH of kanamycin A were modified in search of new aminoglycosides to overcome resistant enzymes, ANTs and APHs. The key intermediate was a dibenzylidene-protected derivative of kanamycin A. T... The 3'-OH, 4'-OH and 2"-OH of kanamycin A were modified in search of new aminoglycosides to overcome resistant enzymes, ANTs and APHs. The key intermediate was a dibenzylidene-protected derivative of kanamycin A. The aimed sites were masked by benzyl, methyl and allyl groups. Multi-step reactions gave the desired aminoglycoside derivatives but showed less antibiotic activity than kanamycin A. 展开更多
关键词 Aminoglycoisdes Kanamycin A derivatives Resistant enzyme Regioselectivity
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Regioselective and Stereoselective Synthesis of the 3-Aryl-4- phosphoryl-1, 2, 4-triazoline-5-ones
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作者 De Xin FENG Ru Yu CHEN You HUANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第9期1145-1148,共4页
A novel and efficient route of synthesizing 1, 2, 4-triazoline-5-ones is reported. The title compounds can be prepared in high yield and purity by the one-pot oxidation and cyclization of 1-acylthiosemicarbazides. The... A novel and efficient route of synthesizing 1, 2, 4-triazoline-5-ones is reported. The title compounds can be prepared in high yield and purity by the one-pot oxidation and cyclization of 1-acylthiosemicarbazides. The reaction is regioselective and stereoselective. The reaction condition is mild. 展开更多
关键词 Triazoline 1-acylthiosemicarbazides regioselective STEREOSELECTIVE cyclization.
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A regioselective synthesis of pentacyclic compounds containing coumarin,pyrrole,indene without catalysts under microwave irradiation
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作者 Zhi-Wei Chen Jun-Bo Hou +1 位作者 Zhao-Ran Dai Xiao-Feng Yang 《Chinese Chemical Letters》 SCIE CAS CSCD 2016年第10期1622-1625,共4页
A concise and efficient approach was developed for the synthesis of pentacyclic compounds containing coumarin, pyrrole, indene in a regioselective manner in good yields via the reactions of N-substituted 4- aminocouma... A concise and efficient approach was developed for the synthesis of pentacyclic compounds containing coumarin, pyrrole, indene in a regioselective manner in good yields via the reactions of N-substituted 4- aminocoumarin compounds and ninhydrin using microwave irradiation. No catalysts are required in our protocol. 展开更多
关键词 4-Aminocoumarin CATALYST-FREE NINHYDRIN regioselective ANNULATION
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Synthesize of 2,6-Di-O-acetyl Sucrose by Regioselective Acetylation with Dibutyltin Oxide
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作者 YuKE MinLIU ZhenZhongLIU 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第3期273-274,共2页
Di-O-acetyl sucrose was regioselective synthesized by using dibutyltin oxide in about 60% yield. The structure of acetyl derivative was elucidated by 1H NMR, 13C NMR, 2D-NMR and MS spectral data.
关键词 Dibutyltin oxide 2 6-di-O-acetyl sucrose regioselective acetylation.
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Regioselective protection of 10-deacetylbaccatin Ⅲ and semi-synthesis of paclitaxel
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作者 Zhang Hu Li Li Ou +1 位作者 Guo Lin Zhang Yong Ping Yu 《Chinese Chemical Letters》 SCIE CAS CSCD 2008年第2期130-132,共3页
Semi-synthesis of paclitaxel was achieved in four steps from 10-deacetylbaccatin HI (10-DAB HI). The key steps are the regioselective protection at the hydroxyl group at C-7 of 10-DAB HI, using 1,1′-thiocarbonyldii... Semi-synthesis of paclitaxel was achieved in four steps from 10-deacetylbaccatin HI (10-DAB HI). The key steps are the regioselective protection at the hydroxyl group at C-7 of 10-DAB HI, using 1,1′-thiocarbonyldiimidazole as a selective reagent, and the deprotection of the protected paclitaxel with a mixture of p-toluenesulfonic acid and 0.1 mol/L aqueous hydrochloride. 展开更多
关键词 PACLITAXEL Protecting group 1 1′-Thiocarbonyldiimidazole regioselective SEMI-SYNTHESIS
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Regioselective Decomposition of 11-Substituted-16α,17α- methyleneazopregna-1,4-dien-3,20-dione
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作者 Bing YANG Jun YANG Ling Ling WENG Hu ZHENG 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第1期12-14,共3页
Regioselective decomposition of 11-substituted- 16α, 17α-methyleneazopregna- 1,4-dien- 3, 20-dione Ⅰ proceeded smoothly through thermal decomposition in the presence of BF3·Et2O or HClO4 with high yields. Ⅰ w... Regioselective decomposition of 11-substituted- 16α, 17α-methyleneazopregna- 1,4-dien- 3, 20-dione Ⅰ proceeded smoothly through thermal decomposition in the presence of BF3·Et2O or HClO4 with high yields. Ⅰ was converted to 11-substituted-16-methylpregna-1, 4, 16(17)-trien-3, 20-dione Ⅱ by the thermal decomposition, while with HClO4 ad a catalyst, 11-substituted-16α, 17α-methylenepregna-1, 4-dien-3, 20-dione Ⅲ was the main product. However, when BF3·Et2O was used as catalyst, a mixture of Ⅱ and Ⅲ(1 : 3) was obtained. 展开更多
关键词 Methyleneazopregnanes methylenepregnancs regioselective decomposition
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Palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring
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作者 Xiai Luo Wenguang Li +4 位作者 Haiyan Lu Guobo Deng Yuan Yang Chunming Yang Yun Liang 《Chinese Chemical Letters》 SCIE CAS CSCD 2021年第2期713-716,共4页
A simultaneous C2-H arylation and C8-H alkylation of naphthalene ring has been achieved by palladiumcatalyzed cascade reaction of N-(2-halophenyl)-2-(naphthalen-1-yl)acrylamides with aryl iodides,which provides an eff... A simultaneous C2-H arylation and C8-H alkylation of naphthalene ring has been achieved by palladiumcatalyzed cascade reaction of N-(2-halophenyl)-2-(naphthalen-1-yl)acrylamides with aryl iodides,which provides an efficient method for synthesizing various aryl-substituted spirocyclic oxindoles.The protocol enables three C-C bonds formation via an intramolecular Heck reaction and sequentially regioselective C-H bond activation. 展开更多
关键词 PALLADIUM-CATALYZED Cascade reaction regioselective C-H activation Naphthalene ring Spirocyclic oxindoles
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DFT Studies on the Origin of Regioselective Ring-opening of Terminal Epoxides during Copolymerization with CO2
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作者 Chuang Liu 罗一 吕小兵 《Chinese Journal of Polymer Science》 SCIE CAS CSCD 2016年第4期439-445,共7页
This report presents a detailed density functional theory (DFT) study on the difference in regioselectivity for the copolymerization reactions of styrene oxide versus propylene oxide with CO2 utilizing binary (sale... This report presents a detailed density functional theory (DFT) study on the difference in regioselectivity for the copolymerization reactions of styrene oxide versus propylene oxide with CO2 utilizing binary (salen)cobalt(III) catalyst systems. This study focuses on the discrepancy of regioselective ring-opening of two terminal epoxides during the copolymerization with CO2. It was found that the nucleophilic ring-opening of styrene oxide occurred predominantly at the methine C a--O bond due to the election delocalization of phenyl group to stabilize the transition state for the methine C--O bond cleavage. 展开更多
关键词 DFT regioselective ring-opening Epoxides.
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THE REGIOSELECTIVE SYNTHESIS OF NOVEL PHENYLSULFONES BEARING ISOPRENE UNITS
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作者 He Sheng ZHANG’ Jia Wei CHEN and Li JIN Department of Chemistry, Hubei University, Wuhan, 430062 《Chinese Chemical Letters》 SCIE CAS CSCD 1993年第5期377-378,共2页
The facile and regioselective synthesis of some novel phenylsulfones bearing isoprene units were accomplished by using the corresponding terpenoid compounds as the starting material through ene-chlorination and phenyl... The facile and regioselective synthesis of some novel phenylsulfones bearing isoprene units were accomplished by using the corresponding terpenoid compounds as the starting material through ene-chlorination and phenylsulfonyl group substritution steps. The yields are excellent and the experimental conditions are very mild. 展开更多
关键词 very THE regioselective SYNTHESIS OF NOVEL PHENYLSULFONES BEARING ISOPRENE UNITS Li CHEN
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