Metathesis Polymerization of Olefins and Polymerization of Alkynes PDF
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Metathesis Polymerization of Olefins and Polymerization of Alkynes NATO ASI Series Advanced Science Institutes Series A Series presenting the results of activities sponsored by the NA TO Science Committee, which aims at the dissemination of advanced scientific and technological knowledge, with a view to strengthening links between scientific communities. The Series is published by an international board of publishers in conjunction with the NATO Scientific Affairs Division A Life Sciences Plenum Publishing Corporation B Physics London and New York C Mathematical and Physical Sciences Kluwer Academic Publishers D Behavioural and Social Sciences Dordrecht, Boston and London E Applied Sciences F Computer and Systems Sciences Springer-Verlag G Ecological Sciences Berlin, Heidelberg, New York, London, H Cell Biology Paris and Tokyo Global Environmental Change PARTNERSHIP SUB-SERIES 1. Disarmament Technologies Kluwer Academic Publishers 2. Environment Springer-Verlag / Kluwer Academic Publishers 3. High Technology Kluwer Academic Publishers 4. Science and Technology Policy Kluwer Academic Publishers 5. Computer Networking Kluwer Academic Publishers The Partnership Sub-Series incorporates activities undertaken in collaboration with NA TO's Cooperation Partners, the countries of the CIS and Central and Eastern Europe, in Priority Areas of concern to those countries. NATO-PCO-DATA BASE The electronic index to the NATO ASI Series provides full bibliographical references (with keywords and/or abstracts) to more than 50000 contributions from international scientists published in all sections of the NATO ASI Series. Access to the NATO-PCD-DATA BASE is possible in two ways: - via online FILE 128 (NATD-PCO-DATA BASE) hosted by ESRIN, Via Galileo Galilei, 1-00044 Frascati, Italy. - via CD-ROM "NATO-PCO-DATA BASE" with user-friendly retrieval software in English, French and German (© WTV GmbH and DATAWARE Technologies Inc. 1989). The CD-ROM can be ordered through any member of the Board of Publishers or through NATO PCO, Overijse, Belgium. Series C: Mathematical and Physical Sciences - Vol. 506 Metathesis Polymerization of Olefins and Polymerization of Alkynes edited by Yavuz Imamoglu Department of Chemistry, Hacettepe University, Ankara, Turkey Springer-Science+Business Media, B.V. Proceedings of the NATO Advanced Study Institute on Ring-opening Metathesis Polymerization of Olefins and Polymerization of Alkynes Akcay-Balikesir, Turkey 3-16 September 1995 A C.I.P. Catalogue record for this book is available from the Library of Congress. ISBN 978-94-010-6183-4 ISBN 978-94-011-5188-7 (eBook) DOI 10.1007/978-94-011-5188-7 Printed an acid-free paper AII Rights Reserved © 1998 Springer Science+Business Media Dordrecht Originally published by Kluwer Academic Publishers in 1998 Softcover reprint of the hardcover 1s t edition 1998 No part of the material protected by this copyright notice may be reproduced or utilized in any form or by any means, electronic or mechanical, including photo copying, recording or by any information storage and retrieval system, without written permission from the copyright owner. TABLE OF CONTENTS PREFACE IX LIST OF PARTICIPANTS xi PART I: METATHESIS POL YMERIZA TION OF OLEFINS: ROMP AND ADMET Rirlg-Opening Metathesis Polymerization by Molybdenum Imido Alkylidene Complexes R.R. Schrock Metathesis of Low-Strain Olefins and Functionalized Olefms with New Ruthenium-Based Catalyst Systems A.F. Noels and A. Demonceau 29 Synthesis of Aryloxide Tungsten (VI) Complexes and their Application in Olefm Metathesis F. Lefebvre, S. Pagano and J-M Basset 47 Novel Catalysts for Addition Polymerization ofNorbomene and its Derivatives K.L. Makovetsky, L.1. Gorbacheva, TG. Golenko, 1. Ya. Ostrovskaya and G.N. Bondarenko 69 The Use of Non-Traditional Catalysts in the ROMP ofCycloolefins K.L. Makovetsky 79 Correlation between Catalyst Nature and Polymer Selectivity in ROMP ofCycloolefms with WC1 -Based Catalytic Systems 6 V. Dragutan, S. Coca and M Dimonie 89 Ring-Opening Metathesis Polymerization of Cycloolefms using Tungsten-Tetraphenylporphyrinate Catalysts V. Dragutan, L. Popescu, S. Coca and M Dimonie 103 Metathesis Ring-Chain Equilibrium in Cyclobutene and I-Methylcyclobutene Systems E. Thorn-Csanyi 117 VI Olefm Cyclopropanation or Olefm Metathesis with Late Transition Metal Complexes? A.F. Noels and A. Demonceau 139 Initiation, Propagation and Termination of Olefm Metathesis Reactions L. Bencze, G. Szalai and R.K. Szilagyi 157 Synthesis of Membrane Materials by ROMP ofNorbomenes ESh. Finkelshtein, EB. Portnykh, K.L. Makovetsky, 1. Ya. Ostrovskaya, NB. Bespalova and Yu.P. Yampolsky 189 Olefm Metathesis in Organosilicon Chemistry ESh. Finkelshtein 201 Side Chain Liquid Crystalline Polymers via ROMP. Influence of Content of Mesogenic Groups and Tacticity on the LC Behaviour M Ungerank, B. Winkler and F. Stelzer 225 Optically Active Polymers via ROMP of Enantiomerically Pure Monomers F. Stelzer, R. Schifter and Th. Steinhausler 243 Synthesis ofWell-Defmed Graft Copolymers via Coupled Living Anionic and Living Ring Opening Metathesis Polymerisation E Khosravi 253 Recent Developments in the Synthesis of Fluorinated Homopolymers and Block Copolymers via Living Ring Opening Metathesis Polymerisation E. Khosravi 265 Formation of Hydrocarbon and Funtionalized Polymers by Acyclic Diene Metathesis (AD MET) Polymerization K.B. Wagener and P.s. Wolfe 277 A New Synthetic Route to Soluble Conjugated Polymers with Valuable Optical Properties P. Kraxner and E. Thorn-Csanyi 297 Metathesis Depolymerization Chemistry as a Means of Recycling Polymers to Telechelics and Fine Organic Chemicals K.B. Wagener, P.s. Wolfe and MD. Watson 309 Quantitative Determination of the Microstructure and Composition of Crosslinked Rubber Blends H.-D. Luginsland and E. Thorn-Csanyi 325 vii Industrial Applications of the Olefm Metathesis Reaction F. Lefebvre and J-M Basset 341 PART II: ALKYNE POLYMERIZATION Living Polymerization of Alkynes by Molybdenum Imido Alkylidene Complexes R.R. Schrock 357 Catalytic Transformation of Alkenes and Alkynes in the Presence of Group 6 Metal Carbonyls T Szymanska-Buzar 381 PART III: MOLECULAR MODELING AND ALKENE POLYMERIZATION Derivatives of Chromocene in Ethylene Polymerisation B R. Messere, A.F. Noels, P. Dournel and J Breulet 393 A Possible Mechanism of Polymer Formation from a,~-Unsaturated Carbonyl Compounds under the Influence of Metathesis Catalytic Systems Ch. Jossifov 403 Molecular Mechanical Modeling of the Metathesis-Active Tungsta Carbenes L. Bencze and R. K. Szilagyi 411 Preface The first NATO Advanced Study Institute on Olefin Metathesis and Polymerization Catalysts was held on September 10-22, 1989 in Akcay, Turkey. Based on the fundamental research of RRSchrock, RGrubbs and K.B.Wagener in the field of ring opening metathesis polymerization (ROMP), acyclic diene metathesis (ADMET) and alkyne polymerization, these areas gained growing interest within the last years. Therefore the second NATO-ASI held on metathesis reactions was on Ring Opening Metathesis Po lymerization of Olefins and Polymerization of Alkynes on September 3-16, 1995 in Akcay, Turkey. The course joined inorganic, organic and polymer chemists to exchange their knowledge in this field. This volume contains the main and short lectures held in Akcay. To include ADMET reactions better into the title of this volume we changed it into: Metathesis Polymerization of Olefins and Alkyne Polymerization. This volume is addressed to research scientists, but also to those who start to work in the area of olefin metathesis and alkyne polymerization. The topics of the course were: mechanism of ROMP reactions/ new catalysts for ROMP/ new products by ROMP/ new catalysts for ADMET/ new products by ADMETI degradation of polymer by metathesis reactions/ alkyne polymerization and metathesis/ industrial application of metathesis reactions. The Advanced Study Institute was generously sponsored by the Scientific Affairs Division of NATO and the editor gratefully acknowledges this sponsorship. We also thank the Members of the Local Organizing Committee for their engagement on a successful NATO-AS!. Yavuz Imamoglu June 1996 IX LIST OF PARTICIPANTS Janos ABONYI University ofVeszprem Veszprem H 8201 PO Box 158 HUNGARY AylaAKKAYA TOOIT AK-SAGE P. K. 16 Mama~ANKARNTURKEY Oliver ARDENT University of Hamburg Institut fur Technische Chemie und Makromolekularer Chemie Buudesstr. 45 20146 Hamburg/GERMANY Eva-Maria AUTH University of Bayreuth Department of Inorganic Chemistry D-95440 Bayreuth/GERMANY Cemil AY DOGDU Hacettepe Dniversitesi Fen Fak. Kimya B61iimii 06532 Beytepe/ ANKARNTURKEY Lajos BENCZE University ofVeszprem Department of Organic Chemistry PO Box 158 H-8201 VeszpremlHUNGARY Sandra BOTZENHARDT University of Bayreuth Department of Inorganic Chemistry D-95440 Bayreuth/GERMANY Cetin BOZKUR T Hacettepe Dniversitesi Fen Fak. Kimya B61iimii 06532 Beytepe/ ANKARNTURKEY Valerian DRAGUTAN Romanian Academy Institute of Organic Chemistry Spl. Indepentei 202 B BucharestlROMANIA Biilent DDz Hacettepe Dniversitesi Fen Fak. Kimya B61iimii 06532 Beytepe/ ANKARA/TURKEY Xl xii Portnykh ELENA B. A.V. Topchiev Inst. of Petrochemical Synthesis Russian Academy of Science 29, Leninsky Prospect 117912 Moscow B-71. RUSSIA Eugene Sh. FINKELSHTEIN A.V. Topchiev Inst. of Petrochemical Synthesis Russian Academy of Science 29, Leninsky Prospect 117912 Moscow B-71. RUSSIA Keriman nONAY DIN Istanbul Teknik Universitesi Fen-Edebiyat Fak. Kimya Bbliimii Maslak 80626 ISTANBUL/TURKEY AliGUNER Hacettepe Universitesi Fen Fak. Kimya Bbliimii 06532 Beytepe/ ANKARAITURKEY Yavuz IMAMOGLU Hacettepe Oniversitesi Fen Fak. Kimya Bbliimii 06532 Beytepe/ ANKARA/TURKEY Ch. JOSSIFOV Institute of Polymers Bulgarian Academy of Science BG 113 SOFIAIBULGARIA Birgiil Z. KARAN Hacettepe Dniversitesi Fen Fak. Kimya Bbliimii 06532 Beytepe/ ANKARAITURKEY CemalKAYA Cumhuriyet Universitesi Fen-Edebiyat Fakultesi Kimya Bbliimii SIV AS/TURKEY Ezat KHOSRAVI University of Durham IRC in Polymer Science and Technology Durham DH 1 3LEIUK Nilgiin KIZILCAN Istanbul Teknik Dniversitesi Fen-Edebiyat Fak. Kimya Bbliimii Maslak 80626 ISTANBUL/TURKEY Jiirgen KaDEL University of Bayreuth Department of Inorganic Chemistry D-9S440 Bayreuth/GERMANY
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