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Reichel Marco.Pdf Dissertation zur Erlangung des Doktorgrades der Fakultät für Chemie und Pharmazie der Ludwig-Maximilians-Universität München SYNTHESIS AND INVESTIGATION OF NEW FLUOROMETHYLATING AGENTS AND THEIR IMPACT ON FORMING ENERGETIC MATERIALS Marco Reichel aus München, Deutschland 2020 Erklärung Diese Dissertation wurde im Sinne von § 7 der Promotionsordnung vom 28. November 2011 von Herrn Professor Dr. Konstantin L. Karaghiosoff betreut. Eidesstattliche Versicherung Diese Dissertation wurde eigenständig und ohne unerlaubte Hilfsmittel erarbeitet. München, den 20.02.2020 ____________________________ MARCO REICHEL Dissertation eingereicht am: 20.02.2020 1. Gutachter: Prof. Dr. Konstantin L. Karaghiosoff 2. Gutachter: Prof. Dr. Thomas M. Klapötke Mündliche Prüfung am: 20.04.2020 ∙−∙∙ First of all, I would like to thank my doctor father, Prof. Dr. Konstantin L. Karaghiosoff, for giving me the opportunity doing my Ph.D. in his research group. I am very grateful that I have been given freedom in the field of research. Further I want to thank Prof. Dr. Konstantin L. Karaghiosoff for my given possibility to participate at several conferences and workshops. I would also express my gratitude for financial support to him. Prof. Dr. Karaghiosoff is one of the most cordial professors with great intellect and vision I have ever met. It was an honor to be able to do my Ph.D. under his guidance. Thank you for the enriching time and for your friendship! Secondly, I would like to thank Prof. Dr. Thomas M. Klapötke for the friendly reception in his chair, the confidence and the support he gave to me. I would also like to express my sincere thanks for taking over the second review of this thesis. I also owe great gratitude to Prof. Dr. Andreas Kornath, without whom this work would not have been possible. Thank you for the great efforts you have made to write proposals together with us. Also thanks for the always enjoyable and generous excursions that we have undertaken. In addition, special thanks go to AOR Dr. Burkhard Krumm to whom I am most grateful for the corrections of several papers and his patience. To Dr. Burkhard Krumm I would like to express my sincere thanks for the great help in writing proposals and in arranging an extremely successful cooperation between the university of Bielefeld. My thanks also go to AOR Dr. Jörg Stierstorfer, who helped me with calculations and with whom a good knowledge transfer regarding tetrazolates resulted. At this point I would also like to thank my cooperation partners Prof. Dr. Norbert Mitzel, Dr. Jan Schwabedissen, Dr. Yuri Vishnevskiy, Dr. Sebastian Blomeyer and Dr. Hans-Georg Stammler for the good and successful cooperation. I thank Dr. Marc Andre Althoff for the informative excursions and the interesting and instructive training at the Bundeswehr in Sonnthofen, which he led. Furthermore, for the friendly conversations, the amusing evenings at conferences and the possibility to work with him. Once again I would like to thank F-Select GmbH especially for the successful cooperation over many years and the industrial donations without which the topic of this dissertation would not have been possible. I would like to thank Ms. Irene Scheckenbach, who with her thoughtful and warm manner is an enrichment for the research group. I want to express my gratitude firstly to the members of the research group of Prof. Dr. Karaghiosoff. To M.Sc. Mara Egenhöfer, I thank you from the bottom of my heart for the wonderful time we spent together. As so often the time is unfortunately always too short, but I will always carry the beautiful moments in my heart. You know best, there are no words that could express my deepest gratitude for this. So I remain with these words: I am proud of you and I hope to see you again! ∙−∙∙ Further I would like to thank M.Sc. Christin Kirst for her tireless efforts to write proposals with me. Thank you for the time and effort you took on me to help me! Also thank you for the funny moments we shared together. Thanks for all. I thank M.Sc. Sarah Linert for her empathy in difficult moments and for the funny moments that have always arisen having you as our group member. Thanks also for the support which I could experience from you. My gratitude goes secondly also to all members of the research group of Prof. Dr. Thomas M. Klapötke. To the former (Dr. Martin Härtel, Dr. Johann Glück, Dr. Marc Bölter, Dr. Thomas Reith) and current (M.Sc. Anne Friedrichs, M.Sc. Cornelia Unger, M.Sc. Teresa Küblböck, M.Sc. Maximilian Wurzenberger, M.Sc. Moritz Kofen, M.Sc. Alicia Dufter, M.Sc. Dominik Dosch, M.Sc. Greta Bikelyte, M.Sc. Max Born, B.Sc. Michael Gruhne, M.Sc. Alexander Harter, M.Sc. Stefanie Heimsch, M.Sc. Marcel Holler, B.Sc. Marcus Lommel, M.Sc. Elena Reinhardt, M.Sc. Maurus Völkl) members. Thanks for your support with measurements, graphic design, for the hospitality after our storage fire, the nice evenings together and for the nice and funny conversations we had together. Thank you for making the work a pleasure. A special thanks goes to Dr. Ivan Gospodinov. Thank you for the great discussions regarding synthetic work and thank you for your friendship! Also I want to express my gratitude to M.Sc. Anne Friedrich for being a great and friendly colleague. M.Sc. Dominik Dosch is thanked for the successful cooperation and for the excurse to the swabian language. In addition, I am grateful to M.Sc. Thomas Schnappinger for helping me with any calculation problems and giving me solutions. Stefan Huber is thanked for his friendly and so helpful manner regarding the sensitivity measurements, joining the ABC-Abwehr team and in general for the nice conversations. In this context I would like to thank my bachelor-, “F-” and master students, by name Freddy Saunders, Hannes Dettlaf, Fabian Huck, Laura Huber, Maximilian Mader, Eduard Wöllner, Martin Obermeier, Alexander Harter, Michael Mertens, Lukas Nusser, Sami Sile, Philipp Schmidt, Nathalie Kurle, Patrick Schüller, Christoph Seifert, Timotheus Hohl, Erol Ceylan, Nina Gordon, Alexander Gisnapp and Kevin Stuke who helped me during my synthetic work. I would like to thank my friends here as well. I would especially like to mention Gabi Wagenstetter, Annette Brandl, Thomas Schnappinger and Maximilian Netter. Thank you for your friendship and your support in all situations of life! Finally, I would like to thank my family from the bottom of my heart! Without your support this work would not have been possible! I thank my mother for her incredible patience with me. Thanks for all you had to endure through me. Without you, I wouldn’t have become a person I am today! I thank my father who taught me everything I am. Thank you for dedicating all of your energies to me in all areas of my life. Even without you, I would never have been as successful as I am allowed to be today. Furthermore, I would like to thank my sister. Thank you for your organizational talent and your empathy, when I just missed the head to anything and thank you for your warm-hearted good nature! I am also grateful for Helmut. With you I have won not only a good friend but also a brother. Thanks that you were always at my side and always cheered me up. Thank you for the beautiful and funny time! Furthermore, I would like to thank my grandparents. You became like second parents for me, who taught me with your wisdom and life experience what it means to become a diligent, honorable and righteous person. Thank you for the wonderful time together which I will never forget! I also thank my uncle and aunt, as well as my cousins with whom I was always allowed to spend a great time. Byoungmoo, I also want to thank you for being like a second dad to me. It is a blessing to have a friend like you, who is an inherent part of the family! And I always consider, 50% of the Nobel Prize ... I am also grateful to be able to number Wolfgang and Erika to our family, with whom we had such beautiful and amusing evenings together, which were so necessary to be able to switch off. Finally, I would like to thank Flauschiwauschi Emma. Thank you for taking away my fears of dogs, for being open for caresses and for the nice time out you took me for a walk. There can never be a better dog! Thank you! Table of Content 1 Introduction ............................................................................................................................. 1 1.1 Overview .......................................................................................................................... 1 1.1.1 Magic of Fluorine ...................................................................................................... 1 1.1.2 Organofluorine Compounds ....................................................................................... 2 1.1.3 References .................................................................................................................. 4 1.2 Reagents for Selective Fluoromethylation – a Challenge in Organofluorine Chemistry .......................................................................................................................... 5 1.2.1 Introduction ................................................................................................................ 6 1.2.1.1 General Overview ............................................................................................ 6 1.2.1.2 Historical Overview of Monofluoromethylating Reagents .............................. 9 1.2.2 Agents for Direct Monofluoromethylation ...............................................................
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