Chemistry of Organic Fluorine Compounds II A Critical Review Milos Hudlicky, Editor Virginia Poiytechnic Institute and State University Attila E. Pavl...
Fluorine is an omnipresent chemical element in our everyday ... catalysis, 2. methodology in ... Journal of Fluorine Chemistry 134 (2012)
y ORGANO-FLUORINE COMPOUNDS B. Baasner BAYER AG, Leverkusen / Germany Editors H. Hagemann ... Reactions of Fluorine in the Gas Phase 193 2.6. Reactions of Fluorine in the Presence of Solvents 194 2.7. Aerosol Fluorination 202 ... Oxidative Desulfuriz
Molecular photoswitches, i.e. molecules capable of isomerizing between two states when submitted to light stimuli, ... high energy metastable photoisomer occurs
Stereochemistry of Organic Compounds ... Resolving Agents 322 b. ... 14. CHIRALITY IN MOLECULES DEVOID OF CHIRAL CENTERS 1119
17. NIR Spectral Correlation Charts 193 18. NIR Band Assignments for Organic Compounds, Polymers, and Rubbers 197 VI. Infrared and Raman Spectroscopy
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
