Title Aromatic fluorination / James H. Clark, David Wails, Tony W. Bastock

Published Boca Raton : CRC Press, Taylor & Francis Group, 2018

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Description 1 online resource : illustrations Series CRC revivals New directions in organic and biological chemistry CRC revivals. New directions in organic and biological chemistry. Contents Cover -- Half Title -- Copyright Page -- Contents -- Chapter 1: Introduction to Aromatic Fluorination -- 1.1 Historical Developments -- 1.2 Properties of Fluorinated Aromatic Molecules -- 1.2.1 Fundamental Properties -- 1.2.2 Effects of Fluorine on Chemical Reactivity -- 1.2.3 Effects of Fluorine on Physical Properties -- 1.3 Applications for Fluorinated Aromatics -- 1.4 Raw Materials -- 1.5 Laboratory and Industrial Methods of Fluorination -- References -- Chapter 2: Halex Chemistry -- 2.1 Introduction -- 2.2 Fluoride Reagents -- 2.2.1 Surface Area -- 2.2.2 Phase Transfer Catalysis and Related Methods -- 2.2.3 Soluble Fluorides -- 2.3 Physical Properties of Fluoroaromatics -- 2.4 Chemical Properties of Fluoroaromatics -- 2.4.1 Nucleophilic Substitution -- 2.4.2 Electrophilic Substitution -- 2.4.3 Radical Substitution -- 2.4.4 Other Chemical Reactivity Effects -- 2.5 Routes to Fluoroaromatics -- 2.5.1 Halex Methods -- 2.5.2 Fluorodenitration Methods -- 2.5.3 Other Aromatic Nucleophilic Fluorinations -- References -- Chapter 3 The Balz-Schiemann Reaction and Related Chemistry -- 3.1 Introduction -- 3.2 Synthesis of Aryldiazonium Tetrafluoroborate Salts -- 3.3 Decomposition of Aryldiazonium Tetrafluoroborate Salts -- 3.4 Alternative Diazonium Salts -- 3.5 Mechanistic Aspects of the Balz-Schiemann Reaction -- 3.6 Fluoroaromatics via HF-Based Diazotizations -- 3.7 Synthetic Methods -- References -- Chapter 4: Other Aromatic Fluorination Methodologies -- 4.1 Introduction -- 4.2 Direct Fluorination -- 4.3 Fluorination Using O-F-Type Compounds -- 4.3.1 Fluoroxytrifluoromethane and Bis(fluoroxy)trifluoromethane -- 4.3.2 Acetyl Hypofluorite -- 4.3.3 Cesium Fluoroxysulfate -- 4.4 Fluorinations Using Xenon Difluoride -- 4.5 Fluorination Using High-Valency Metal Fluorides -- 4.5.1 Silver (11) Fluoride -- 4.5.2 Cobalt Trifluoride 4.6 Electrochemical Fluorination -- 4.7 Fluorination Using N-F-Type Reagents -- 4.8 Miscellaneous Fluorination Methods -- 4.9 Synthetic Methods -- References -- Chapter 5 Trifluoromethylaromatics -- 5.1 Introduction -- 5.2 Physical Properties -- 5.3 Chemical Properties -- 5.4 Synthesis of Trifluoromethylated Aromatics -- 5.4.1 Routes from Toluenes Using Hydrogen Fluoride and Related Reactions -- 5.4.2 Routes from Haloaromatics Using Organometallic Reagents -- 5.4.3 Routes from Aromatic Hydrocarbons -- 5.4.4 Routes from Aromatic Carboxylic Acids -- 5.4.5 Routes from Other Aromatic Substrates -- 5.5 Synthetic Methods -- References -- Chapter 6 Trifluoromethylthioaromatics and Trifluoromethylsulfonylaromatics -- 6.1 Introduction -- 6.2 Physical Properties of Trifluorornethylthioaromatics and Trifluoromethylsulfonylaromatics -- 6.3 Chemical Properties of Trifluorornethylthioaromatics and Trifluoromethylsulfonylaromatics -- 6.4 Synthesis of Trifluoromethylthioaromatics and Trifluoromethylsulfonylaromatics -- 6.4.1 Routes to Trifluoromethylthioaromatics from Arylmethyl Sulfides via the Trichloromethylthioaromatics -- 6.4.2 Routes to Trifluorornethylthioaromatics from Haloaromatics via Nucleophilic Substitution -- 6.4.3 Routes to Trifluoromethylthioaromatics from Aromatic Hydrocarbons via Electrophilic Substitution -- 6.4.4 Routes to Trifluoromethylthioaromatics from Aromatic Thiols via Radical Substitution -- 6.4.5 Routes to Trifluorornethylsulfonylaromatics from Aromatic Hydrocarbons via Electrophilic Substitution -- 6.4.6 Routes to Trifluorornethylsulfonylaromatics from Trifluoromethylthioaromatics via Oxidation -- 6.4.7 Routes to Trifluorornethylsulfonylaromatics from other Aromatic Substrates -- 6.5 Synthetic Methods -- References -- Chapter 7 Other Aromatic Ring Substituents -- 7.1 Introduction -- 7.2 Physical Properties -- 7.3 Chemical Properties 7.4 Synthesis of Trifluoromethoxy-Substituted Aromatics -- 7.4.1 Halogen Exchange Reactions of Î, Î, Î -Trichloromethoxy Aromatics -- 7.4.2 Conversion of Phenols to Trifluoromethoxybenzenes -- 7.5 Synthesis of Fluoroalkoxy-Substituted Aromatics -- 7.6 Synthesis of Perfluoroalkyl-Substituted Aromatics -- 7.6.1 Direct Incorporation of Perfluoroalkyl Groups -- 7.6.2 Fluorination of Existing Side Chains -- 7.6.3 Nucleophilic Substitution Reactions -- 7.7 Synthesis of Fluoroalkyl-Substituted Aromatics -- 7.8 Synthesis of Aryl Difluoromethyl Ethers and Thioethers -- 7.9 Synthetic Methods -- 7.9.1 Trifluoromethoxy-Substituted Aromatics -- 7.9.2 Fluoroalkoxy-Substituted Aromatics -- 7.9.3 Perfluoroalkyl-Substituted Aromatics -- 7.9.4 Fluoroalkyl-Substituted Aromatics -- 7.9.5 Aryl Difluoromethyl Ethers and Thioethers -- References -- Chapter 8 Industrial Aspects of Aromatic Fluorine Chemistry -- 8.1 Introduction -- 8.2 The Demand for Aromatic Fluorine Compounds -- 8.3 The Supply of Aromatic Fluorine Compounds -- 8.4 Industrial Methods -- 8.5 Industrial Products -- 8.6 Key Intermediates and Synthetic Routes -- References -- Index Summary "Academia and industry join forces in Aromatic Fluorination, as an expert from each domain contributes to this new text on fluorination of carbocyclic and heterocyclic rings. The book begins with a discussion of fluorine's unique combination of properties, including size, electronic effects, and hydrophobicity, as well as the historical development of its product applications. It explains methods for introducing fluorine into an aromatic ring, focusing on nucleophilic fluorine transfer reactions. The role of catalysts, solvents, and other variables are examined, and the scope and limitations of the methods are discussed. Of particular interest to those working in non-specialist laboratories, Aromatic Fluorination includes detailed descriptions of the new electrophilic routes to fluoroaromatics, in addition to traditional routes and alternative methods involving radical chemistry. Because one of the most important fluorine-containing substituent is CF3, the book explains routes to benzotrifluorides (ArCF3), including traditional industrial methods and modern alternatives employing C-1 halofluorocarbons and other fluoroaliphatics. An alternative to CF3 is CF3S, and several methods of synthesizing aromatic CF3S-containing molecules are described. Since the successful development and diverse applications of aromatic fluorine compounds have led to the search for new compounds and novel substituents, the incorporation of other substituents is also explored. Aromatic Fluorination concludes with discussion of the factors responsible for the successful development of pharmaceutical, agrochemical and liquid crystal applications and the potential for applications in high-performance polymers and other areas. This section also describes in detail important industrial aromatic fluorination processes and the relative merits of different process technologies and their costs."--Provided by publisher Notes "First published 1996 by CRC Press ... Reissued 2018 by CRC Press"--Title page verso Bibliography Includes bibliographical references and index Notes Online resource; title from PDF title page (EBSCO, viewed January 23, 2018) Subject Aromatic fluorine compounds. Fluorination. Fluoridation SCIENCE -- Chemistry -- Organic. Aromatic fluorine compounds Fluorination Hydrocarbures aromatiques. Fluoro-carbones. Fluoruration industrielle. Aromaticité. Fluorine. Fluoration. Composés aromatiques fluorés. Fluor -- Composés organiques. Form Electronic book Author Wails, David, author. Bastock, T. W., author. ISBN 9781351078337 135107833X 9781351069885 1351069888 9781351086783 1351086782 9781351095235 1351095234

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