Chinese Journal of Chemistry

Cover image for Vol. 30 Issue 1

January, 2012

Volume 30, Issue 1

Pages 1–204

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Masthead
    4. Editorial
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    8. Communication
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    10. Notes
    11. Erratum
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      Cover Picture: Asymmetric Synthesis of Both Enantiomers of Disparlure (Chin. J. Chem. 1/2012) (page 1)

      Zhigang Wang, Jianfeng Zheng and Peiqiang Huang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201290000

      Thumbnail image of graphical abstract

      The cover picture shows a new and expeditious approach for the synthesis of disparlure and its enantiomer. The disparlure is the sex pheromone of the Gypsy moth Porthetria dispar L., which is used to monitor the Gypsy moth and protect plants against these pests. Starting from propargyl alcohol, and on the basis of Zhou's modified Sharpless asymmetric epoxidation, the sex pheromone of the Gypsy moth, disparlure and its enantiomer have been synthesized, each in six steps, with overall yields of 29% and 27% (ee>98%), respectively. The use of the sequential coupling tactic renders the method flexible, which is applicable to the synthesis of other cis-epoxy pheromones. More details are discussed in the article by Zheng et al. on page 23–28.

  2. Masthead

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    1. Masthead (page 2)

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201290002

  3. Editorial

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      Chinese Journal of Chemistry: Entering the Third Decade in 2012 (pages 3–4)

      Guozhen Ji and Shengming Ma

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201290003

  4. Contents

    1. Top of page
    2. Cover Picture
    3. Masthead
    4. Editorial
    5. Contents
    6. Further Masthead Information
    7. Full Paper
    8. Communication
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    10. Notes
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  5. Further Masthead Information

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    3. Masthead
    4. Editorial
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    8. Communication
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    1. Further Masthead Information (page 14)

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201290001

  6. Full Paper

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    1. Direct α-Alkylation of Aldehydes by Brønsted-Acid Catalysis (pages 15–18)

      Xiangrong Zhu, Ting Wang and Qixiang Guo

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100464

      Thumbnail image of graphical abstract

      A Brønsted acid-catalyzed direct alkylation reaction of aldehydes was described. The 3,5-dinitrobenzoic acid promoted the reaction between aldehydes and diarylmethanols to afford the corresponding alkylation products with middle to high yields (up to 91% yield).

  7. Communication

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    1. Effect of Device Fabrication Conditions on Photovoltaic Performance of Polymer Solar Cells Based on Poly(3-hexylthiophene) and Indene-C70 Bisadduct (pages 19–22)

      Guangjin Zhao, Youjun He, Bo Peng and Yongfang Li

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201100145

      Thumbnail image of graphical abstract

      Power conversion efficiency of the polymer solar cells based on poly(3-hexylthiophene) (P3HT) as donor and indene-C70 bisadduct (IC70BA) as acceptor reached 5.82% with open circuit voltage of 0.81 V, short circuit current of 11.37 mA/cm2 and fill factor of 64.0%, under the irradiation of AM1.5, 100 mW/cm2, at the optimized conditions of 188-nm-thick active layer of P3HT:IC70BA (1:1, w:w) blend film and pre-thermal annealing at 150°C for 10 min.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Masthead
    4. Editorial
    5. Contents
    6. Further Masthead Information
    7. Full Paper
    8. Communication
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    10. Notes
    11. Erratum
    1. Asymmetric Synthesis of Both Enantiomers of Disparlure (pages 23–28)

      Zhigang Wang, Jianfeng Zheng and Peiqiang Huang

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100482

      Thumbnail image of graphical abstract

      Starting from propargyl alcohol (12), and on the basis of Zhou's modified Sharpless asymmetric epoxidation, the sex pheromone of the Gypsy moth, disparlure (+)-8 and its enantiomer (−)-8 have been synthesized, each in six steps, with overall yields of 29% for (+)-8 and 27% for (−)-8 (ee>98%). The use of the sequential coupling tactic renders the method flexible, which is applicable to the synthesis of other cis-epoxy pheromones.

    2. CuCl-Catalyzed Aerobic Oxidation of Allylic and Propargylic Alcohols to Aldehydes or Ketones with 1:1 Combination of Phenanthroline and Bipyridine as the Ligands (pages 29–34)

      Yu Liu and Shengming Ma

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201100476

      Thumbnail image of graphical abstract

      A series of allylic and propargylic alcohols were oxidized to the corresponding aldehydes or ketones using molecular oxygen in air as the oxidant and CuCl with 1:1 combination of phenanthroline and bipyridine as the catalyst system.

    3. Synthesis and Anti-tumor Evaluation of B-ring Modified Caged Xanthone Analogues of Gambogic Acid (pages 35–42)

      Xiang Li, Xiaojin Zhang, Xiaojian Wang, Nianguang Li, Changjun Lin, Yuan Gao, Zhuoqin Yu, Qinglong Guo and Qidong You

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100045

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      Two new series of B-ring modified caged xanhone analogues of Gambogic acid analogues were designed and synthesized utilizing a Claisen/Diel-Alder cascade reaction. These compounds were evaluated for their in vitro anti-tumor activities against A549, MCF-7, SMMC-7721 and BGC-823 cancer cell lines by MTT assay. The structure-activity relationship (SAR) was also discussed.

    4. Molecularly Imprinted Polymer for Solid-Phase Extraction of Ecteinascidin 743 from Sea Squirt (pages 43–46)

      Minglei Tian, Shengnan Li and Kyungho Row

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180450

      Thumbnail image of graphical abstract

      Ecteinascidin 743 from sea squirt is one of the most original anti-tumoral activity compounds, as proven by the Natural Cancer Institute. Ecteinascidin 743 could be obtained with traditional liquid extraction, but it should be purified and separated from the extract. A molecularly imprinted solid-phase extraction procedure was developed for the selective separation.

    5. Orthogonal Enzymatic Reactions to Control Supramolecular Hydrogelations (pages 53–58)

      Guoqin Chen, Chunhua Ren, Ling Wang, Bing Xu and Zhimou Yang

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100082

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      A small molecular hydrogel could be manipulated by two enzymes, phosphatase for the formation of gels and esterase for the gel-sol phase transitions.

    6. A New Nanocatalytic Spectrophotometric Assay for Cationic Surfactant Using Phosphomolybdic Acid-Formic Acid-Nanogold as Indicator Reaction (pages 59–64)

      Zhiliang Jiang, Huimin Qin and Aihui Liang

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100061

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      NG has a strong catalysis on the PMo blue colored reaction, but the NGA catalysis is weak. With the increase of CS concentration, the NG decreased, and the PMo blue absorption value at 700 nm decreased linearly. Thus the CS can be determined spectrophotometrically.

    7. A Green Route for the One-Pot Synthesis of 1,2-Disubstituted Benzimidazoles Using Iron(III) Phosphate under Solventless Conditions (pages 65–70)

      F. K. Behbahani and Parisa Ziaei

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180461

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      1,2-Disubstituted benzimidazoles are selectively synthesized in high yields under extremely mild conditions via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of iron(III) phosphate under solvent-free conditions. The use of readily available iron(III) phosphate as a reusable and recyclable catalyst makes this process quite simple, convenient, and environment-friendly.

    8. Synthesis, Structure Elucidation and H+/K+-ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives (pages 71–76)

      Nianyu Huang, Lei Chen, Zhaojiang Liao, Hubiao Fang, Junzhi Wang and Kun Zou

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100051

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      Nine bisabolangelone reduction derivatives were synthesized and characterized. Preliminarily H+/K+-ATPase activity evaluation indicated compounds II and IV exhibited better inhibitory activities against H+/K+-ATPase than bisabolangelone and the commercial omeprazole with the IC50 of 23.21 and 65.32 μmol/L, respectively.

    9. Synthesis and Antimicrobial Activity of New 2,5-Disubstituted 1,3,4-Oxadiazoles and 1,2,4-Triazoles and Their Sugar Derivatives (pages 77–83)

      Wael A. El-Sayed, Omar M. Ali, Hend A. Hendy and Adel A.-H. Abdel-Rahman

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100029

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      A series of new 2,5-disubstituted-1,3,4-oxadiazole and 1,2,4-triazole derivatives were synthesized by heterocyclization of acid hydrazide 1 and thiosemicarbazide derivative 2. Furthermore the acyclic C-nucleoside analogs were also prepared by cyclization of their corresponding sugar hydrazones by reaction with acetic anhydride.

    10. Theoretical Study of the Radical Scavenging Activity of Shikonin and Its Derivatives (pages 84–90)

      Ruifa Jin and Jie Li

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100044

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      The radical scavenging activity of shikonin has been theoretically investigated. Six shikonin derivatives have been designed by introducing different groups with the aim to design good candidates for radical scavenging activity.

    11. Photochemical Studies on 5-Methylbicyclo[1.1.1]pentane Derivatives: p-Orbital Overlap Controlled Enantioselectivity (pages 91–95)

      Manling Ma, Chao Yang, Bing Li, Yutian Shao, Guolei Zhao and Wujiong Xia

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201100083

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      The first example of the p-orbital overlap controlled enantioselectivity of Norrish type II photocyclization reaction was described. Irradiation of 5-methyl bicyclo[1.1.1]pentanyl ketone with UV in the solid state as well as in the acetonitrile solution afforded the Norrish/Yang photocyclization compound as the sole product. Solid-state asymmetric photochemical studies using ionic chiral auxiliary technique led to the enantioselectivity as high as 60%. The results were rationalized by X-ray single crystal structure.

    12. A Facile One-pot Synthesis of α-Halo,α-allylic Aldehydes from α,α-Dihalo Ketones Utilizing Allylic Zinc Bromide (pages 96–102)

      Xiaolei Wang and Songlin Zhang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180466

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      An efficient synthesis of various α-halo,α-allylic aldehydes from α,α-dihalo ketones using both cyclic (3-bromocyclohex-1-ene zinc bromide and (Z)-3-bromocyclobut-1-ene zinc bromide) and acyclic (allylzinc bromide and cinnamylzinc bromide) type of allylic organozinc bromide with DMF as base is described. A possible reaction mechanism is also proposed.

    13. Electrochemiluminescence of SDBS-Ru(bpy)32+-CPM System and Its Application (pages 103–108)

      Lijun Li, Wenyan Gao, Wenyi Huang, Zhuo Cai, Dachun Hu and Yanqing Li

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100012

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      The additions of surfactants have obvious influence to the electrochemical and electrochemiluminescence (ECL) intensity of Ru(bpy)32+-chlorpheniramine maleate (CPM) system at the Au electrode. When the concentration of SDBS is 0.7 mmol·L−1, enhancement of the ECL intensity was 14-fold at Au electrode. Base on this, an ECL method was established for efficient and simple determination of CPM at Au electrode with high sensitivity and wide linear range. The enhanced effect of SDBS on ECL intensity of other eleven kinds of tertiary amines-Ru(bpy)32+ systems was universal in either GC electrode or Au electrode, while the enhancement of ECL intensity was higher in Au electrode than that in GC electrode.

    14. Kinetics of the Reaction of 2-Chloro-3,5-dinitrobenzotriflouride with Aniline in Toluene and Methanol-Toluene Mixed Solvents (pages 109–114)

      Magda F. Fathalla

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180467

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      Kinetics of the reaction of 2-chloro-3,5-dinitrobenzotriflouride with aniline was studied in toluene, methanol-toluene binary solvents, benzene and chloroform. The reaction in toluene exhibits third-order kinetics consistent with aggregates of aniline.

    15. Molecular Dynamics Simulation of Diffusion of Vitamin C in Water Solution (pages 115–120)

      Jianping Zeng, Aimin Wang, Xuedong Gong, Jingwen Chen, Song Chen and Feng Xue

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180459

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      Under different temperatures and concentrations, the diffusion of Vitamin C (VC) in water solution was examined by molecular dynamics simulation. The diffusion coefficients were calculated based on the Einstein equation. The influences of temperature, concentration, and simulation time on the diffusion coefficient were discussed.

    16. DFT Studies of Ag-Loading Intrinsic and Functionalized Single-Walled Carbon Nanotubes (pages 121–126)

      Zhuxia Zhang, Yaxian Hao, Liping Wang, Minghui Dong, Wensheng Hou, Peide Han, Xuguang Liu and Bingshe Xu

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180449

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      The first principles study was performed on the stability of Ag adsorbed on the internal walls of single-walled carbon nanotube (SWCNT) and loaded on acid modified SWCNT. The calculation results show that Ag can be adsorbed stably on the internal walls of SWCNT.

      Corrected by:

      Erratum: Erratum: DFT Studies of Ag-Loading Intrinsic and Functionalized Single-Walled Carbon Nanotubes

      Vol. 30, Issue 5, 1192, Article first published online: 15 MAY 2012

    17. Photocatalytic Degradation of Imidacloprid by Phosphotungstic Acid Supported on a Mesoporous Sieve MCM-41 (pages 127–132)

      Changgen Feng, Yanzhou Li and Xia Liu

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180453

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      Solid catalysts consisting of polyoxometalates (POM) namely phosphotungstic acid H3PW12O40 (HPW) supported on a mesoporous sieve MCM-41 have been prepared and characterized. The HPW/MCM-41 with different HPW loadings from 10 to 60 wt% possess large specific surface area and rather uniform mesopores. Keggin structure of HPW retains on the prepared composite catalysts. The photocatalytic performance of HPW/MCM-41 was examined by degradation of a durable pesticide imidacloprid. It is found that the prepared photocatalysts exhibit high activity under irradiation of 365 nm monochromatic light.

    18. Molecular and Mesoscopic Dynamics Simulations on the Compatibility of PLA/Plasticizer Blends (pages 133–138)

      Jie Jing, Qing'an Qiao, Yueqing Jin, Cuihua Ma, Honglan Cai, Yanfeng Meng, Zhengting Cai and Dacheng Feng

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180454

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      The compatibility of the blend systems for olyactic acid (PLA)/tributyl citrate (TBC) and PLA/glycerol has been studied by molecule and mesoscopic dynamics methods. The results from glass transition temperature simulations showed that the compatibility of PLA/TBC system was better than that of PLA/glycerol, which were consistent with the conclusion obtained from the pair correlation functions. Besides, the behaviors of phase state distribution and evolution process were investigated by mesoscopic dynamics method as well. The results indicated that citrate ester was a better plasticizer than glycerol for PLA.

    19. β-Alanine-DBU: A Highly Efficient Catalytic System for Knoevenagel-Doebner Reaction under Mild Conditions (pages 139–143)

      Lingjian Zhu, Ning Lei, Zhenyuan Miao, Chunquan Sheng, Chunlin Zhuang, Jianzhong Yao and Wannian Zhang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180455

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      A mild and efficient Knoevenagel-Doebner reaction from malonic acid and a wide range of aldehydes was catalyzed by a catalytic system consisting of β-alanine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), affording the corresponding (E)-α,β-unsaturated carboxylic acids in good to excellent yields and with high stereoselectivity. The advantage of the method is that the reaction could proceed smoothly at ambient temperature so that it can tolerate a variety of functional groups and avoid unnecessary side reactions.

    20. Preparation of Mesoporous 1,4-Phenylene-silica Nanorings through a Dual-templating Approach (pages 144–150)

      Weike Zhu, Baozong Li, Lifeng Bi, Sibing Wang, Wei Zhuang, Yi Li and Yonggang Yang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180464

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      Mesoporous 1,4-phenylene-silica nanorings were prepared using cetyltrimethylammonium bromide (CTAB) and (S)-2-methyl-1-butanol as a chiral dopant in concentrated aqueous NH3 solutions. Transmission electron microscopy images of the samples indicated that the nanorings were formed by bending nanorods 360(. With increasing the stirring speed or the (S)-2-methyl-1-butanol/CTAB molar ratio, the morphologies of mesoporous 1,4-phenylene-silicas changed from helical nanofibers to nanorings, and then to nano-saddles. Circular dichroism spectra of these hybrid silicas indicated that they were chiral.

    21. Nanoporous Pt Catalyst Modified by Sn Electrodeposition for Electrochemical Oxidation of Formaldehyde (pages 151–156)

      Qingfeng Yi and Gekunkun Zuo

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180457

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      A novel titanium-supported nanoporous Pt catalyst (nanoPt/Ti) was fabricated using a hydrothermal method and the nanoPt/Ti electrode was then modified with limited amounts of tin particles generated by cyclic potential scans to synthesize a Sn-modified nanoporous Pt catalyst (Sn/nanoPt/Ti). Compared to nanoPt/Ti, formaldehyde electrooxidation on Sn/nanoPt/Ti displays a dramatic improvement at the most negative potentials.

    22. Evaluation and Comparison of a 3,5-Dimethylphenyl Isocyanate Teicoplanin with Phenyl Isocyanate Teicoplanin Chiral Stationary Phase Using RP-HPLC (pages 157–162)

      Baochun Shen, Datong Zhang, Xiaoyan Yu, Wei Guo, Yaqiong Han and Xiuzhu Xu

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180463

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      Two chiral stationary phases (CSP), phenylisocyanate teicoplanin CSP (Phe-TE), and 3,5-dimethylphenyl isocyanate teicoplanin CSP (DMP-TE) were prepared from the macrocyclic glycopeptide teicoplanin CSP (TE) using derivative agents, phenyl isocyanate or 3,5-dimethylphenyl isocyanate, respectively. The evaluation and comparison of these two self-made CSP were performed using HPLC enantiomeric separations. Eight α-amino acids reached enantioseparation using the RPLC mobile phase. The chiral selectivity factor for six α-amino acids on DMP-TE is somewhat bigger than that on Phe-TE CSP under RP mode.

    23. Fabrication of a Sensitive Electrochemical Biosensor for Detection of DNA Hybridization Based on Gold Nanoparticles/CuO Nanospindles Modified Glassy Carbon Electrode (pages 167–172)

      Yuzhong Zhang, Mingzhu Wang and Lei Huang

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180451

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      In this work, a sensitive electrochemical DNA biosensor for the detection of sequence- specific target DNA was reported.

    24. A Novel Sandwich-type Dinuclear Complex for High-capacity Hydrogen Storage (pages 173–176)

      Haiyan Zhu, Yuanzhen Chen, Sai Li, Xiuzhen Cao and Yongning Liu

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180462

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      From density functional theory calculations, we predicted that the sandwich-type dinuclear organometallic compounds Cp2Ti2 and Cp2Sc2 can adsorb up to eight hydrogen molecules respectively, corresponding to a high gravimetric storage capacity of 6.7% and 6.8% (w), respectively. These sandwich-type organometallocenes are favorable for reversible adsorption and desorption of hydrogen at ambient conditions.

    25. Synthesis, Characterization and Ion Exchange Properties of a New Composite of Inorganic Ion Exchanger: Polyacrylonitrile Cerium(IV) Molybdophosphate (pages 177–182)

      Seyed Javad Ahmadi, Ramin Yavari, Parviz Ashtari, Vanik Gholipour, Leila Kamel and Farokh Rakhshandehru

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180456

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      Cerium(IV) molybdophosphate (CMP) as an inorganic ion exchanger and polyacrylonitrile (PAN) as a binder were used to prepare the granular composite of the CMP-PAN. The distribution coefficients of some metal ions were obtained. Finally, it was used for decontamination of low level liquid waste.

    26. Spectrofluorimetric and Spectrophotometric Stability-Indicating Methods for the Analysis of Veralipride in Presence of Its Degradants and in Spiked Human Plasma (pages 183–189)

      Nahla Nour El Din Ahmed Salama, Maissa Yacoub Salem, Lobna Mohammed Abd El Halim and Laila El-Sayed Abdel Fattah

      Article first published online: 16 JAN 2012 | DOI: 10.1002/cjoc.201180465

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  9. Notes

    1. Top of page
    2. Cover Picture
    3. Masthead
    4. Editorial
    5. Contents
    6. Further Masthead Information
    7. Full Paper
    8. Communication
    9. Full Papers
    10. Notes
    11. Erratum
    1. N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones (pages 190–194)

      Lihui Sun, Tong Wang and Song Ye

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100383

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      An N-heterocyclic carbene-catalyzed [2+2+2] annulation reaction of allenoates with two molecules of trifluoromethylketone is reported, which is different from the corresponding [3+2] and [2+2] reaction catalyzed by phosphines and amines, respectively.

    2. Synthesis of 2,2-Bis-C-functionalized Chain Glucosid-3-ketals (pages 195–198)

      Fuyi Zhang, Hong Liu, Yingming Sheng and Hongmin Liu

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201180431

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    3. Methenamine as an Efficient Ligand for Copper-catalyzed Coupling of Phenols with Aryl Halides (pages 199–203)

      Cunwei Qian, Qianshou Zong and Dong Fang

      Article first published online: 23 DEC 2011 | DOI: 10.1002/cjoc.201100077

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      Methenamine was found to be an efficient, inexpensive and facile ligand for the CuX-catalyzed O-arylation of phenols with aryl iodides and bromides. The present protocol is applicable to a variety of phenols and aryl iodides containing electron-withdrawing, electron-donating, and sterically demanding substrate combinations under mild conditions.

  10. Erratum

    1. Top of page
    2. Cover Picture
    3. Masthead
    4. Editorial
    5. Contents
    6. Further Masthead Information
    7. Full Paper
    8. Communication
    9. Full Papers
    10. Notes
    11. Erratum
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