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Competitive aromatic carbon fluorine and carbon hydrogen bond activation by iridium(iii) porphyrins.

Chan, Chung Yin. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2011. / Includes bibliographical references (leaves 77-80). / Abstracts in English and Chinese. / Table of Contents --- p.i / Acknowledgements --- p.iii / Abbreviations --- p.V / Abstract --- p.vi / Chapter Chapter 1 - --- Introduction --- p.1 / Chapter 1.1 --- Definition of Aromatic Bond Activation --- p.1 / Chapter 1.2 --- History of Carbon-Fluorine Bond Activation --- p.1 / Chapter 2.2.1 --- Examples of Aromatic Carbon-Fluorine Bond Activation in 1970s --- p.1 / Chapter 2.2.2 --- Examples of Aromatic Carbon-Fluorine Bond Activation in 1980s --- p.2 / Chapter 2.2.3 --- Examples of Aromatic Carbon-Fluorine Bond Activation in 1990s --- p.3 / Chapter 2.2.4 --- Examples of Aromatic Carbon-Fluorine Bond Activation in 2000s --- p.6 / Chapter 1.3 --- Difficulties and Challenges in Aromatic Bond Activation Applications of Aromatic Carbon Fluorine Bond Activation --- p.6 / Chapter 2.2.1 --- Thermodynamic Estimations --- p.7 / Chapter 2.2.2 --- Competitive Aromatic Bond Activation --- p.9 / Chapter 1.3.2.1 --- Competitive Aromatic Carbon-Hydrogen and Carbon-Halogen Bond Activation --- p.10 / Chapter 1.3.2.2 --- Competitive Aromatic Carbon-Hydrogen and Carbon-Fluorine Bond Activation --- p.15 / Chapter 1.4 --- Mechanistic Investigations of Aromatic CFA --- p.17 / Chapter 2.2.1 --- Oxidative Addition --- p.17 / Chapter 2.2.2 --- Nucleophilic Aromatic Substitution --- p.18 / Chapter 2.2.3 --- Fluorine Atom Abstraction --- p.19 / Chapter 2.2.4 --- "1,2-Addition" --- p.19 / Chapter 1.5 --- Mechanistic Investigations of Aromatic Carbon-Hydrogen Bond Activation --- p.20 / Chapter 2.2.1 --- Oxidative Addition --- p.20 / Chapter 2.2.2 --- Electrophilic Aromatic Substitution --- p.21 / Chapter 2.2.3 --- "1,2-Addition" --- p.21 / Chapter 1.6 --- Applications of Aromatic Carbon-Fluorine Bond Activation --- p.22 / Chapter 1.7 --- Applications of Aromatic Carbon-Hydrogen Bond Activation --- p.23 / Chapter 1.8 --- Structural Features of Iridium Porphyrins --- p.23 / Chapter 1.9 --- Obj ectives of the Work --- p.25 / Chapter Chapter 2 - --- Competitive Aromatic Carbon Fluorine and Carbon Hydrogen Bond Activation by Iridium(III) Porphyrins --- p.26 / Chapter 2.1 --- C-F Activation of Fluorobenzene by Rhodium(III) Porphyrins --- p.26 / Chapter 2.2 --- Preparation of Starting Materials --- p.26 / Chapter 2.2.1 --- Preparation of Tetratolylporphyrin --- p.26 / Chapter 2.2.2 --- Preparation of Iridium(III) Porphyrin Carbonyl Chloride --- p.27 / Chapter 2.3 --- Base Effect of Carbon-Fluorine Bond Activation --- p.27 / Chapter 2.4 --- Solvent Effect of Carbon-Fluorine Bond Activation --- p.30 / Chapter 2.5 --- Temperature Effect --- p.31 / Chapter 2.6 --- Concentration Effect of Carbon-Fluorine Bond Activation --- p.33 / Chapter 2.7 --- Activations of Fluorobenzenes --- p.33 / Chapter 2.8 --- Electronic Effect --- p.36 / Chapter 2.9 --- Mechanistic Studies --- p.38 / Chapter 2.9.1 --- Activation of Fluorobenzene --- p.38 / Chapter 2.9.2 --- Reaction between Ir(ttp)H and Fluorobenzene --- p.40 / Chapter 2.9.3 --- Reaction between Ir2(ttp)2 and Fluorobenzene --- p.41 / Chapter 2.9.4 --- "Reaction between Ir(ttp)""K+ and Fluorobenzene" --- p.42 / Chapter 2.9.5 --- Reaction between Ir(ttp)Me and Fluorobenzene --- p.44 / Chapter 2.10 --- Proposed Mechanism for CFA --- p.45 / Chapter 2.11 --- Proposed Mechanism for CHA --- p.47 / Chapter 2.12 --- Kinetic and Thermodynamic CFA and CHA Products --- p.47 / Chapter 2.13 --- Summary --- p.48 / Chapter Chapter 3 - --- Experimental Section --- p.49 / Reference --- p.77 / Chapter Appendix I - --- Spectra --- p.81

Identiferoai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_327449
Date January 2011
ContributorsChan, Chung Yin., Chinese University of Hong Kong Graduate School. Division of Chemistry.
Source SetsThe Chinese University of Hong Kong
LanguageEnglish, Chinese
Detected LanguageEnglish
TypeText, bibliography
Formatprint, vi, 91 leaves : ill. ; 30 cm.
RightsUse of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/)

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