Chemistry of Organic Fluorine Compounds II

Chemistry of Organic Fluorine Compounds II A Critical Review Milos Hudlicky, Editor Virginia Poiytechnic Institute and State University Attila E. Pavl...

0 downloads 143 Views 1MB Size
Chemistry of Organic Fluorine Compounds II A Critical Review Milos Hudlicky, Editor Virginia Poiytechnic Institute and State University

Attila E. Pavlath, Editor Agricultural Research Service, U. S. Department of Agriculture

ACS Monograph 187 American Chemical Society Washington, DC 1995

CONTENTS

Preface

xiii

How To Use This Book

xv

Abbreviations

xvii

Procedures

xix

Contributors

xxi

1

Survey of the Literature of Organic Fluorine Chemistry Milos Hudlicky and Atüla E. Pavlath

2

Survey of Fluorinating Agents Dayal T. Meshri

3

Methods of Introducing Fluorine into Organic Molecules Addition of Fluorine Suzanne T. Purrington

1

23

41

Addition of Hydrogen Fluoride Andrew E. Feiring

54

Addition of Halogen Fluorides to Unsaturated Systems Andrew E. Feiring

61

Addition of Fluorine and Other Elements Andrew E. Feiring

70

Replacement of Hydrogen by Fluorine James L. Adcock

97

Replacement by Means of High-Valency Fluorides Milos Hudlicky

120

Electrophilic Fluorination of Carbon-Hydrogen Bonds Timothy B. Patrick

133

Replacement of Halogens by Fluorine Donald F. Halpern and Gerald G. Vernice Replacement of Oxygen by Fluorine W. Dmowski

172

ix

199

4

Replacement of Sulfur by Fluorine W. Dmowski

263

Replacement of Nitrogen by Fluorine MaxM. Boudaklan

271

Reactions of Organic Fluorine Compounds Reduction C. G. Krespan

297

Oxidation Oldrich Paleta

321

Halogenation S. R. Elsheimer

364

Nitration G. L. Cantrell and J. F. Lang

387

Nitrosation G. L. Cantrell and J. F. Lang

398

Sulfonation G. L. Cantrell and J. F. Lang

403

Acid-Catalyzed Syntheses G. L. Cantrell and J. F. Lang

408

Hydrolysis W. H. Gumprecht Alkylation C. Wakselman

422 446

Fluorocarbene Insertions R. L. Soulen

497

Arylation Timothy B. Patrick

501

Acylation R. W. Lang

525

Fluorinated Sulfur, Phosphorus, Boron, and Silicon Compounds J. T. Welch and Seniz Turner-McMullin Base-Catalyzed Condensations J. T. Welch

545

Reactions of Fluoromagnesium and Fluorolithium Compounds C. Tamborski Other Organometallic Syntheses Donald J. Burton andZhen-Yu Yang Additions: Linear Additions across Double Bonds L. G. Sprague, K. B. Baucom, S. F. Seilers, and R. A. DuBoisson x

615 646 670 729

Linear Additions to Acetylenic Compounds R, L. Soulen

757

Cycloadditions Forming Three- and Four-Membered Rings B. E. Smart

767

Cycloadditions Forming Five- and Six-Membered Rings W. R. Dolbier Addition Reactions across Polyfluoroalkyl- and PerfluoroalkylSubstituted CO and CN Multiple Bond Systems K. Burger, N. Sewald, C. Schierlinger, and E. Brunner

797

Eliminations M. Hudlicky and A. E. Pavlath

888

Molecular Rearrangements and Pyrolysis H. Koroniak

913

5

Fluorinated Compounds as Reagents Peter J. Stang and Viktor V. Zhdankin

939

6

Properties of Fluorinated Compounds Physical and Physicochemical Properties B. E. Smart Biological Properties R. Filier and K. Kirk

7

979 1011

Analysis of Organic Fluorine Compounds Destructive Analytical Methods Dayal T. Meshri Modern Methods of Separation, Identification, and Structure Determination Mark L. Robin Nuclear Magnetic Resonance Spectroscopy of Organofluorine Compounds T. Stephen Everett

8

840

Applications of Fluorinated Compounds Refrigerants, Propellants, and Foam-Blowing Agents R. L. Powell Fire Suppression Agents Mark L. Robin Organic Fluoropolymers W. W. Schmiegel XI

1023

1029

1037

1089 1099 1101

Fluorinated Pharmaceuticals Arthur J. Elliott 18 F-Labeled Radiopharmaceuticals D. F. Holpern

1119 1126

Fluorinated Anesthetics L. L. Ferstandig

1133

Perfluorinated Liquids in Biology and Medicine L. C. Clark

1138

Fluorinated Agrochemicals R. W. Lang

1143

Author Index

1149

Subject Index

1247

Xll