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254 Topics in Current Chemistry Editorial Board: A.de Meijere · K.N.Houk · H.Kessler · J.-M.Lehn · S.V.Ley S.L.Schreiber · J.Thiem · B.M.Trost · F.Vögtle · H.Yamamoto Topics in Current Chemistry Recently Published and Forthcoming Volumes Anion Sensing Natural Product Synthesis I Volume Editor:Stibor,I. Volume Editor:Mulzer,J. Vol.255,2005 Vol.243,2005 Organic Solid State Reactions Immobilized Catalysts Volume Editor:Toda,F. Volume Editor:Kirschning,A. Vol.254,2005 Vol.242,2004 DNA Binders and Related Subjects Transition Metal and Rare Earth Volume Editors:Waring,M.J.,Chaires,J.B. Compounds III Vol.253,2005 Volume Editor:Yersin,H. Contrast Agents III Vol.241,2004 Volume Editor:Krause,W. The Chemistry ofPheromones Vol.252,2005 and Other Semiochemicals II Chalcogenocarboxylic Acid Derivatives Volume Editor:Schulz,S. Volume Editor:Kato,S. Vol.240,2005 Vol.251,2005 The Chemistry ofPheromones New Aspects in Phosphorus Chemistry V and Other Semiochemicals I Volume Editor:Majoral,J.-P. 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Volume Editors:Gütlich,P.,Goodwin,H.A. Vol.244,2005 Vol.233,2004 Organic Solid State Reactions Volume Editor: Fumio Toda With contributions by D.Braga · D.D’Addario · S.Giaffreda · F.Grepioni · W.Jones G.Kaupp · K.Komatsu · L.Maini · A.Matsumoto · M.Polito M.Sakamoto · J.R.Scheffer · F.Toda · A.V.Trask · W.Xia 3 The series Topics in Current Chemistrypresents critical reviews ofthe present and future trends in modern chemical research.The scope ofcoverage includes all areas ofchemical science including the interfaces with related disciplines such as biology,medicine and materials science.The goal ofeach thematic volume is to give the nonspecialist reader,whether at the university or in industry,a comprehensive overview ofan area where new insights are emerging that are ofinterest to a larger scientific audience. As a rule,contributions are specially commissioned.The editors and publishers will,however,always be pleased to receive suggestions and supplementary information.Papers are accepted for Topics in Current Chemistry in English. In references Topics in Current Chemistryis abbreviated Top Curr Chem and is cited as a journal. Visit the TCC content at springerlink.com Library ofCongress Control Number:2004110638 ISSN 0340-1022 ISBN 3-540-22982-5Springer Berlin Heidelberg New York DOI 10.1007/b98357 This work is subject to copyright.All rights are reserved,whether the whole or part ofthe material is con- cerned,specifically the rights oftranslation,reprinting,reuse ofillustrations,recitation,broadcasting,repro- duction on microfilms or in any other ways,and storage in data banks.Duplication ofthis publication or parts thereofis only permitted under the provisions ofthe German Copyright Law ofSeptember 9,1965,in its cur- rent version,and permission for use must always be obtained from Springer-Verlag.Violations are liable to prosecution under the German Copyright Law. 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Cover design:KünkelLopka,Heidelberg/design & production GmbH,Heidelberg Typesetting:Fotosatz-Service Köhler GmbH,Würzburg Printed on acid-free paper02/3141 xv – 5 4 3 2 1 0 Volume Editor Prof.Dr.Fumio Toda Department ofChemistry Okayama University ofScience, Ridai-cho 1-1 Okayama 700-0005,Japan [email protected] Editorial Board Prof.Dr.Armin de Meijere Prof.K.N.Houk Institut für Organische Chemie Department ofChemistry and Biochemistry der Georg-August-Universität University ofCalifornia Tammannstraße 2 405 Hilgard Avenue 37077 Göttingen,Germany Los Angeles,CA 90024-1589,USA [email protected] [email protected] Prof.Jean-Marie Lehn Prof.Dr.Horst Kessler Institut de Chimie Institut für Organische Chemie Université de Strasbourg TU München 1 rue Blaise Pascal,B.P.Z 296/R8 Lichtenbergstraße 4 67008 Strasbourg Cedex,France 85747 Garching,Germany [email protected] [email protected] Prof.Stuart L.Schreiber Prof.Steven V.Ley Chemical Laboratories University Chemical Laboratory Harvard University Lensfield Road 12 Oxford Street Cambridge CB2 1EW,Great Britain Cambridge,MA 02138-2902,USA [email protected] [email protected] Prof.Barry M.Trost Prof.Dr.Joachim Thiem Department ofChemistry Institut für Organische Chemie Stanford University Universität Hamburg Stanford,CA 94305-5080,USA Martin-Luther-King-Platz 6 [email protected] 20146 Hamburg,Germany [email protected] Prof.Hisashi Yamamoto Arthur Holly Compton Distinguished Prof.Dr.Fritz Vögtle Professor Kekulé-Institut für Organische Chemie Department ofChemistry und Biochemie der Universität Bonn The University ofChicago Gerhard-Domagk-Straße 1 5735 South Ellis Avenue 53121 Bonn,Germany Chicago,IL 60637 [email protected] 773-702-5059,USA [email protected] Topics in Current Chemistry also Available Electronically For all customers who have a standing order to Topics in Current Chemistry, we offer the electronic version via SpringerLink free ofcharge.Please contact your librarian who can receive a password for free accessto the full articles by registration at: springerlink.com If you do not have a subscription,you can still view the tables of contents of the volumes and the abstract of each article by going to the SpringerLink Homepage,clicking on “Browse by Online Libraries”,then “Chemical Sciences”, and finally choose Topics in Current Chemistry. You will find information about the – Editorial Board – Aims and Scope – Instructions for Authors – Sample Contribution at springeronline.com using the search function. Preface Organic reactions in the absence of solvent, so called “Organic Solid-State Reactions”,have been well established as proceeding much more efficiently and faster than solution reactions in many cases,since solid-state reactions are infinitely high-concentration reactions.Organic solid-state reactions proceed even more selectively than solution reactions in some cases,since substrate molecules in solids or crystals are ordered regularly.Solid-state reactions are important not only for their high efficiency and selectivity but also for their simplicity and cleanness.In other words,solid state reactions may be regarded as more economical and ecologically favorable procedures in chemistry. Organic solid-state reactions are also useful for studying molecular dynam- ics,since dynamic behavior ofmolecules in the solid-state can easily be moni- tored by spectral measurements and X-ray analysis. For example, reaction mechanisms can easily be clarified by studying molecular dynamics in the solid state. In this volume,thermochemical and photochemical reactions in the solid state which have been studied mainly during the last five years by eight research groups are included.The editor hopes that this volume will contribute to the further development oforganic solid-state reactions and solid-state chemistry. Fumio Toda Okayama,November 2004 Contents Thermal and Photochemical Reactions in the Solid-State F.Toda . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 Crystal Engineering ofOrganic Cocrystals by the Solid-State Grinding Approach A.V.Trask · W.Jones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 Intra-Solid and Inter-Solid Reactions ofMolecular Crystals: a Green Route to Crystal Engineering D.Braga · D.D’Addario · S.L.Giaffreda · L.Maini · M.Polito · F.Grepioni 71 Organic Solid-State Reactions with 100% Yield G.Kaupp . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95 The Mechanochemical Solid-State Reaction ofFullerenes K.Komatsu . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185 Photochemical Aspects ofThiocarbonyl Compounds in the Solid-State M.Sakamoto . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207 Asymmetric Induction in Organic Photochemistry via the Solid-State Ionic Chiral Auxiliary Approach J.R.Scheffer · W.Xia . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233 Reactions of1,3-Diene Compounds in the Crystalline State A.Matsumoto . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263 Author Index Volumes 201–254 . . . . . . . . . . . . . . . . . . . . . . . . 307 Subject Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 309 Contents of Volume 248 Templates in Chemistry I Volume Editors:Christoph A.Schalley · Fritz Vögtle · Karl Heinz Dötz ISBN 3-540-22547-1 Spacer-Controlled Multiple Functionalization ofFullerenes C.Thilgen · S.Sergeyev · F.Diederich Chromium-Templated Benzannulation and Haptotropic Metal Migration K.H.Dötz · B.Wenzel · H.C.Jahr Supramolecular Templating in the Formation ofHelicates M.Albrecht Hydrogen-Bond-Mediated Template Synthesis ofRotaxanes,Catenanes, and Knotanes C.A.Schalley · T.Weilandt · J.Brüggemann · F.Vögtle Template-Controlled Synthesis in the Solid-State L.R.MacGillivray · G.S.Papaefstathiou · T.Friščić· D.B.Varshney · T.D.Hamilton Gels as Templates for Nanotubes J.H.Jung · S.Shinkai Contents of Volume 249 Templates in Chemistry II Volume Editors:Christoph A.Schalley · Fritz Vögtle · Karl Heinz Dötz ISBN 3-540-23087-4 First Considerations:Principles,Classification,and History D.H.Busch Macrocycle Synthesis Through Templation Z.R.Laughrey · B.C.Gibb Macrocycles and Complex Three-Dimensional Structures Comprising Pt(II) Building Blocks A.Kaiser · P.Bäuerle Templated Synthesis ofInterlocked Molecules F.Aricó · J.D.Badjic · S.J.Cantrill · A.H.Flood · K.C.F.Leung · Y.Liu · J.F.Stoddart Molecular Knots C.Dietrich-Buchecker · B.X.Colasson · J.-P.Sauvage Templation in Noncovalent Synthesis ofHydrogen-Bonded Rosettes M.Crego-Calama · D.N.Reinhoudt · M.G.J.ten Cate Imprinted Polymers A.J.Hall · M.Emgenbroich · B.Sellergren
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