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Page 1: Graphical Abstracts

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Journal of Fluorine Chemistry 147 (2013) iv–vi

Contents lists available at ScienceDirect

Journal of Fluorine Chemistry

journal homepage: www.elsevier .com/locate/ f luor

Graphical Abstracts/J. Fluorine Chem. 147 (2013) iv–vi

Peculiarities of cyclization of ethyl 2-ethoxymethylene-3-oxo-3-(polyfl uoroalkyl)propionates with 3-amino-5-hydroxypyrazoleMarina V. Goryaeva, Yanina V. Burgart, Viktor I. Saloutin

I.Ya. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 620990 Ekaterinburg, Russian Federation

� Ethyl 2-ethoxymethylene-3-oxo-3-(polyfl uoroalkyl)propionates react with 3-amino-5-hydroxypyrazole to give dihydropyrazolo[1,5-a]pyrimidines. � Dihydropyrazolo[1,5-a]pyrimidines undergo recyclization to form pyrazolo[3,4-b]pyridines and are dehydrated to pyrazolo[1,5-a]pyrimidines. � Non-fl uorinated 2-ethoxymethylene-3-oxo esters in the reactions with 3-amino-5-hydroxypyrazole form only pyrazolo[1,5-a]pyrimidines.

J. Fluorine Chem., 147 (2013) 15

Synthesis of FSO2CF2CF2OCF2I from difl uoro(fl uorosulfonyl)acetyl fl uoride and its relevant salt FSO2CF2CF2O�K� in the presence of I2 or CF2I2

Jolanta Ignatowskaa, Oleg Shyshkovb, Klaus Hintzerb, Gerd-Volker Röschenthalera

aSchool of Engineering and Science, Jacobs University Bremen GmbH, Campus Ring 1, D-28759 Bremen, Germany bDyneon GmbH, D-84504 Burgkirchen Werk Gendorf, Germany

� The reaction of diiododifl uoromethane with fl uorinated alkoxide.� The reaction of difl uorocarbene with fl uorinated alkoxide. � The synthesis of fl uorinated telomers.

J. Fluorine Chem., 147 (2013) 10

Aromatic fl uoro-de-triazenation with boron trifl uoride diethyl etherate under non-protic acid conditionsMitja Kovacab, Marko Anderluhb, Johnny Vercouilliea, Denis Guilloteaua, Patrick Emonda, Sylvie Mavela

aUniversité François-Rabelais de Tours, INSERM U930, CHRU, Hôpital Bretonneau, Service de Médecine Nucléaire, 37000 Tours, France bUniversity of Ljubljana, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Askerceva 7, 1000 Ljubljana, Slovenia

� Fluorination of 3,3-diethyl-1-(4-substituted aryl)triazenes. � Fluoro-de-triazenation methodology using boron trifl uoride under conventional and microwave heating in different organic solvents. � Absence of protic acid, thus avoiding the competitive formation of the unwanted compound Ar-A.

J. Fluorine Chem., 147 (2013) 5


Page 2: Graphical Abstracts

Graphical Abstracts v

Multidimensional NMR characterization of perfl uorinated monomer and its precursorsBo Zhanga, Linlin Lia, Frantisek Mikesb, Yasuhiro Koikec, Yoshiyuki Okamotob, Peter L. Rinaldia

aDepartment of Chemistry, University of Akron, 190 E. Buchtel Commons, Akron, OH 44325-3601, USA bPolymer Research Institute, Polytechnic Institute of New York University, Six Metro Tech Center, Brooklyn, NY 11201, USA cFaculty of Science and Technology, Keio Photonics Research Institute, Keio University, Yokohama 223-8522, Japan

� Selective COSY and NOESY were used to study perfl uorinated monomer and its precursors. � Modifi ed gHSQC 2D NMR was used to give two-bond 19F–13C correlations. � Quantitative 1H or 19F 1D NMR experiments were conducted to calculate the isomer ratios.

J. Fluorine Chem., 147 (2013) 40

Fuorinated hydrogen bonding liquid crystals based on Schiff baseZhilian Liuab, Jian Zhanga, Tengfei Lia, Zhenning Yua, Shuxiang Zhangab

aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China bShandong Key Laboratory of Fluorine Chemistry and Chemical Engineering Materials, Jinan 250022, China

� We synthesized new schiff base with fl uoroalkoxy as the terminal chains. � The corresponding supramolecular liquid crystals show good mesomorphic properties. � Wide mesomorphic phase ranges and high order were found. � The corresponding supramolecular liquid crystals show smectic A phase. � However, the analogs with alkoxy terminal chains show nematic phase.

J. Fluorine Chem., 147 (2013) 36

6-Polyfl uoroalkylated 2-thiouracils in the synthesis of pyrimido [2,1-b][1,3,5]thiadiazines by the double Mannich reactionOl’ga G. Khudinaa, Anna E. Ivanovaa, Yanina V. Burgarta, Victor I. Saloutina, Marionella A. Kravchenkob

aPostovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22/20, S. Kovalevskoy/Akademicheskaya Street, 620990 Ekaterinburg, Russia bPhthisiopulmonology Research Institute, Ministry of Public Health of the Russian Federation, 50, 22 Parts’ezda Street, 620039 Ekaterinburg, Russia

� 6-Polyfl uoroalkyl-2-thiouracils react with formaldehyde and primary amines to produce pyrimido[2,1-b][1,3,5]thiadiazines via the multicomponent double Mannich reaction. � The use of ethylenediamine in these reactions results in the product of the bis-double Mannich cyclocondensation. � 8-Polyfl uoroalkyl-pyrimido[2,1-b]thiadiazines exhibit weak tuberculostatic activity.

J. Fluorine Chem., 147 (2013) 31

On the reactions of trialkyl(trifl uorovinyl)silanes with isocyanates and isothiocyanates � Expected and surprising resultsNatalia V. Kirija, Wieland Tyrrab, Harald Schererc, Yurii L. Yagupolskiia, Ingo Pantenburgb, Dieter Naumannb

aInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, UA-02094 Kiev, Ukraine bInstitut für Anorganische Chemie, Universität zu Köln, Greinstraße 6, D-50939 Köln, Germany cInstitut für Anorganische und Analytische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, D-79104 Freiburg, Germany

� Amides of 2,3,3-trifl uoroacrylic and 2,3,3-trifl uorothioacrylic acids were prepared by a one-pot procedure. � The behaviour of the synthesized amides towards fl uoride ions was studied. � Amides of 2,3,3,3-tetrafl uoropropionic and 2,3,3,3-tetrafl uorothiopropionic acids and cyclic products with the �-lactam structure have been synthesized.

J. Fluorine Chem., 147 (2013) 22




















Page 3: Graphical Abstracts

vi Graphical Abstracts

N,N-dialkyl perfl uoroalkanesulfonamides: Synthesis, characterization and propertiesShi-Tao Fu, Shuai-Ling Liao, Jin Nie, Zhi-Bin Zhou

Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China

� A series of N,N-dialkyl perfl uoroalkanesulfonamides were synthesized in high quality and good yields. � The infl uences of structure variation on their fundamental physicochemical properties were extensively studied. � These compounds showed relatively low melting points even lower than �40 °C. � These compounds showed high polarity comparable to that of short chain alcohols.

J. Fluorine Chem., 147 (2013) 56

New approach to synthesize �,�-difl uorohomoallylic alcoholsMasaaki Omote, Tatsuya Miake, Atsushi Tarui, Kazuyuki Sato, Itsumaro Kumadaki, Akira Ando

Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata 573-0101, Japan

� Ethyl 4,4-difl uoro-3-(triethylsilyl)but-3-enoate (3) was synthesized. � 3 generates 4,4-difl uorocarbanion by treatment of 3 with TBAF. � The generated 4,4-difl uorocarbanion attacks to aldehydes. � 3 serves good building block for constructing �,�-difl uorohomoallylic alcohols.

J. Fluorine Chem., 147 (2013) 1

Synthesis and characterization of a novel difunctional fl uorinated acrylic oligomer used for UV-cured coatingsZhenlong Yanab, Weiqu Liua, Nan Gaoab, Ziqi Maab, Minjian Hanab

aGuangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China bUniversity of Chinese Academy of Sciences, Beijing 100049, China

� A novel difunctional fl uorinated oligomer (MATHFA) was successfully prepared. � The fi lm containing 1.3 wt.% of MATHFA exhibits very high hydrophobic surfaces. � XPS confi rmed that longer fl uorinated chain was easier migration to the air-side. � The modifi ed fi lms can maintain the bulk properties due to low amount of MATHFA.

J. Fluorine Chem., 147 (2013) 49