Superacid Chemistry by George A. Olah Second Edition

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Superacid Chemistry by George A. Olah Second Edition

Superacid Chemistry by George A. Olah Second Edition

Free Download Superacid Chemistry by George A. Olah Second Edition

Superacid Chemistry



George A. Olah

G. K. Surya Prakash

Arpad Molnar

Jean Sommer




More than 20 years passed since the publication of our book on Superacids. The book became out of print and much progress since was made in the field, which is gaining increasing interest and significance. Hence, it seems warranted to provide the interested reader with a comprehensively updated review and discussion of the field with literature coverage until early 2008. The title has been changed to ‘‘Superacid

Chemistry” to reflect enormous progress in the field. Some aspects of super-electrophilic activation are also discussed (for more elaborate coverage, readers are referred to G. A. Olah and D. A. Klump, ‘‘Superelectrophiles and Their Chemistry”

Wiley-Interscience, 2008). Our friend and colleague, Arpad Molnar joined us as a coauthor and made an outstanding contribution to the revised new edition of our book, which we hope will be of interest and use to the chemical community. Our publisher is thanked for arranging the new revised edition.


Table of Contents

Preface to the Second Edition xvii

Preface to the First Edition xix

  1. General Aspects 1

1.1. Defining Acidity 1

1.2. Definition of Superacids 6

1.3. Types of Superacids 9

1.4. Experimental Techniques for Acidity Measurements (Protic Acids) 11

  1. Superacid Systems 35

2.1. Primary Superacids 35

2.2. Binary Superacids 47

2.3. Ternary Superacids 62

2.4. Solid Superacids 63

  1. Carbocations in Superacid Systems 83

3.1. Introduction 83

3.2. Methods of Generating Carbocations in Superacids Systems 87

3.3. Methods and Techniques in the Study of Carbocations 88

3.4. Trivalent Carbocations 93

3.5. Equilibrating (Degenerate) and Higher (Five or Six)

Coordinate (Nonclassical) Carbocations 206

  1. Heterocations in Superacid Systems 311

4.1. Introduction 311

4.2. Onium Ions 311

4.3. Enium Ions 397

4.4. Homo- and Heteropolyatomic Cations 426

4.5. Cations of Group 6–12 Elements 453

4.6. Miscellaneous Cations 460

  1. Superacid-Catalyzed Reactions 501

5.1. Conversion of Saturated Hydrocarbons 501

5.2. Alkylation of Aromatic Hydrocarbons 554

5.3. Acylation of Aromatics 608

5.4. Carboxylation 618

5.5. Formylation 627

5.6. Thio- and Dithiocarboxylation 632

5.7. Sulfonation and Sulfonylation 633

5.8. Nitration 636

5.9. Nitrosonium Ion (NO

5.10. Halogenation 647

5.11. Amination 659

5.12. Oxyfunctionalization 660

5.13. Superacids in Protection Group Chemistry 676

5.14. Superacids in Heterocyclic Chemistry 680

5.15. Dehydration 698

5.16. Superacids in Carbohydrate Chemistry 700

5.17. Rearrangements and Cyclizations 706

5.18. Ionic Hydrogenation 727

5.19. Esterification and Ester Cleavage 734

5.20. Additions 735

5.21. Ritter Reactions 742

5.22. Polymerization 744

5.23. Miscellaneous Reactions 750

References 756

Outlook 789

Index 791


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Superacid Chemistry by George A. Olah Second Edition

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