Richard H. Wiley, University of Louisville, Louisville, Kentucky.Paul Wiley, Upjohn Laboratories, Kalamazoo, Michigan.

• Part 1. ChemistryChapter I. General1. Introduction 32. Historical 43. Structure 54. Synthesis 95. Physical Properties 106. Chemical Properties 11Chapter II. Pyrazolin-5-ones1. Introduction 132. Unsubstituted Alkyl, Alicyclic, Aralkyl, Aryl and Heterocyclic Substituted Derivatives 13A. 2-Pyrazolin-5-ones 13(1) Syntheses 13(2) Physical Properties 18(3) Chemical Properties 19(4) Hydroxyalkyl Types 29(5) Aminoalkyl Types 30(6) Bis(2-pyrazolin-5-ones) 31B. 2-Pyrazolin-5-thiones 40C. 5-Imino-2-pyrazolines 41D. 3-Pyrazolin-5-ones 46(1) Syntheses 46(2) Properties 49(3) Bis(3-pyrazoIin-5-ones) 56E. 3-Pyrazolin-5-thiones and -5-selenones 58F. 5-Imino-3-pyrazolines 593. Hydroxy and Mercapto Derivatives 61A. 2-Pyrazolin-5-ones 61B. 3-Pyrazolin-5-ones 634. Amino, Imino, Hydrazino, Azo and Related Derivatives 65A. 2-Pyrazolin-5-ones 65B. 3-Pyrazolin-5-ones 765. Halogen Substituted Derivatives 81A. 2-Pyrazolin-5-ones 81B. 3-Pyrazolin-5-ones 836. Nitroso Substituted Derivatives 85A. 2-Pyrazolin-5-ones 85B. 3-Pyrazolin-5-ones 877. Nitro Substituted Derivatives 88A. 2-Pyrazolin-5-ones 88B. 3-Pyrazolin-5-ones 898. Aldehydes and Ketones 89A. 2-Pyrazolin-5-ones 89B. 3-Pyrazolin-5-ones 929. Carboxylic Acids and Derivatives 95A. 2-Pyrazolin-5-ones 95B. 3-Pyrazolin-5-ones 10010. Sulfonic Acids and Derivatives 101A. 2-Pyrazolin-5-ones 101B. 3-Pyrazolin-5-ones 10211. Functional Group Substituents on Nitrogen 102A. 2-Pyrazolin-5-ones 102B. 3-Pyrazolin-5-ones 10+12. Mercury Substituted Derivatives 104A. 2-Pyrazolin-5-ones 104B. 3-Pyrazolin-5-ones 10513. Metallic and Non-metallic Complexes 105A. 2-Pyrazolin-5-ones 105B. 3-Pyrazolin-5-ones 10714. Miscellaneous Derivatives 108Chapter III. 2-Pyrazolin-4-ones IllChapter IV. 2-Pyrazolin-4,5-diones 114Chapter V. 3-Pyrazolidinones 115Chapter VI. 3,4-Pyrazolidinediones 120Chapter VII. 3,5-Pyrazolidinediones1. Introduction 1232. Alkyl, Aralkyl, Heterocyclicalkyl and Aryl Substituted Derivatives 1243. Hydroxy and Alkoxy Substituted Derivatives 1284. Amino and Azo Substituted Derivatives 1285. Halogen Substituted Derivatives 1296. Nitroso Substituted Derivatives 1297. C-Acyl Substituted Derivatives 1298. N-Acyl Substituted Derivatives 130Chapter Vlll. 5-Imino-3-pyrazolidinones1. Introduction 1312. Alkyl, Alicyclic, Aralkyl, Heterocyclicalkyl, Heterocyclic and Aryl Substituted Derivatives 1323. Functional Group Derivatives 137Chapter IX. Miscellaneous 3,5-Pyrazolidinediones and Analogs 139Part 2. ApplicationsChapter I. Medical 143Chapter II. Color Photography 148Chapter III. Textile and Fabric Dyes 152Chapter IV. Analytical Reagents 155Chapter V. Miscellaneous 157Appendix. Systematic Tables of Pyrazolones and their Derivatives 161References 483Index 525

Richard H. Wiley, University of Louisville, Louisville, Kentucky.Paul Wiley, Upjohn Laboratories, Kalamazoo, Michigan.

• Part 1. ChemistryChapter I. General1. Introduction 32. Historical 43. Structure 54. Synthesis 95. Physical Properties 106. Chemical Properties 11Chapter II. Pyrazolin-5-ones1. Introduction 132. Unsubstituted Alkyl, Alicyclic, Aralkyl, Aryl and Heterocyclic Substituted Derivatives 13A. 2-Pyrazolin-5-ones 13(1) Syntheses 13(2) Physical Properties 18(3) Chemical Properties 19(4) Hydroxyalkyl Types 29(5) Aminoalkyl Types 30(6) Bis(2-pyrazolin-5-ones) 31B. 2-Pyrazolin-5-thiones 40C. 5-Imino-2-pyrazolines 41D. 3-Pyrazolin-5-ones 46(1) Syntheses 46(2) Properties 49(3) Bis(3-pyrazoIin-5-ones) 56E. 3-Pyrazolin-5-thiones and -5-selenones 58F. 5-Imino-3-pyrazolines 593. Hydroxy and Mercapto Derivatives 61A. 2-Pyrazolin-5-ones 61B. 3-Pyrazolin-5-ones 634. Amino, Imino, Hydrazino, Azo and Related Derivatives 65A. 2-Pyrazolin-5-ones 65B. 3-Pyrazolin-5-ones 765. Halogen Substituted Derivatives 81A. 2-Pyrazolin-5-ones 81B. 3-Pyrazolin-5-ones 836. Nitroso Substituted Derivatives 85A. 2-Pyrazolin-5-ones 85B. 3-Pyrazolin-5-ones 877. Nitro Substituted Derivatives 88A. 2-Pyrazolin-5-ones 88B. 3-Pyrazolin-5-ones 898. Aldehydes and Ketones 89A. 2-Pyrazolin-5-ones 89B. 3-Pyrazolin-5-ones 929. Carboxylic Acids and Derivatives 95A. 2-Pyrazolin-5-ones 95B. 3-Pyrazolin-5-ones 10010. Sulfonic Acids and Derivatives 101A. 2-Pyrazolin-5-ones 101B. 3-Pyrazolin-5-ones 10211. Functional Group Substituents on Nitrogen 102A. 2-Pyrazolin-5-ones 102B. 3-Pyrazolin-5-ones 10+12. Mercury Substituted Derivatives 104A. 2-Pyrazolin-5-ones 104B. 3-Pyrazolin-5-ones 10513. Metallic and Non-metallic Complexes 105A. 2-Pyrazolin-5-ones 105B. 3-Pyrazolin-5-ones 10714. Miscellaneous Derivatives 108Chapter III. 2-Pyrazolin-4-ones IllChapter IV. 2-Pyrazolin-4,5-diones 114Chapter V. 3-Pyrazolidinones 115Chapter VI. 3,4-Pyrazolidinediones 120Chapter VII. 3,5-Pyrazolidinediones1. Introduction 1232. Alkyl, Aralkyl, Heterocyclicalkyl and Aryl Substituted Derivatives 1243. Hydroxy and Alkoxy Substituted Derivatives 1284. Amino and Azo Substituted Derivatives 1285. Halogen Substituted Derivatives 1296. Nitroso Substituted Derivatives 1297. C-Acyl Substituted Derivatives 1298. N-Acyl Substituted Derivatives 130Chapter Vlll. 5-Imino-3-pyrazolidinones1. Introduction 1312. Alkyl, Alicyclic, Aralkyl, Heterocyclicalkyl, Heterocyclic and Aryl Substituted Derivatives 1323. Functional Group Derivatives 137Chapter IX. Miscellaneous 3,5-Pyrazolidinediones and Analogs 139Part 2. ApplicationsChapter I. Medical 143Chapter II. Color Photography 148Chapter III. Textile and Fabric Dyes 152Chapter IV. Analytical Reagents 155Chapter V. Miscellaneous 157Appendix. Systematic Tables of Pyrazolones and their Derivatives 161References 483Index 525

Richard H. Wiley, University of Louisville, Louisville, Kentucky.Paul Wiley, Upjohn Laboratories, Kalamazoo, Michigan.

• Part 1. ChemistryChapter I. General1. Introduction 32. Historical 43. Structure 54. Synthesis 95. Physical Properties 106. Chemical Properties 11Chapter II. Pyrazolin-5-ones1. Introduction 132. Unsubstituted Alkyl, Alicyclic, Aralkyl, Aryl and Heterocyclic Substituted Derivatives 13A. 2-Pyrazolin-5-ones 13(1) Syntheses 13(2) Physical Properties 18(3) Chemical Properties 19(4) Hydroxyalkyl Types 29(5) Aminoalkyl Types 30(6) Bis(2-pyrazolin-5-ones) 31B. 2-Pyrazolin-5-thiones 40C. 5-Imino-2-pyrazolines 41D. 3-Pyrazolin-5-ones 46(1) Syntheses 46(2) Properties 49(3) Bis(3-pyrazoIin-5-ones) 56E. 3-Pyrazolin-5-thiones and -5-selenones 58F. 5-Imino-3-pyrazolines 593. Hydroxy and Mercapto Derivatives 61A. 2-Pyrazolin-5-ones 61B. 3-Pyrazolin-5-ones 634. Amino, Imino, Hydrazino, Azo and Related Derivatives 65A. 2-Pyrazolin-5-ones 65B. 3-Pyrazolin-5-ones 765. Halogen Substituted Derivatives 81A. 2-Pyrazolin-5-ones 81B. 3-Pyrazolin-5-ones 836. Nitroso Substituted Derivatives 85A. 2-Pyrazolin-5-ones 85B. 3-Pyrazolin-5-ones 877. Nitro Substituted Derivatives 88A. 2-Pyrazolin-5-ones 88B. 3-Pyrazolin-5-ones 898. Aldehydes and Ketones 89A. 2-Pyrazolin-5-ones 89B. 3-Pyrazolin-5-ones 929. Carboxylic Acids and Derivatives 95A. 2-Pyrazolin-5-ones 95B. 3-Pyrazolin-5-ones 10010. Sulfonic Acids and Derivatives 101A. 2-Pyrazolin-5-ones 101B. 3-Pyrazolin-5-ones 10211. Functional Group Substituents on Nitrogen 102A. 2-Pyrazolin-5-ones 102B. 3-Pyrazolin-5-ones 10+12. Mercury Substituted Derivatives 104A. 2-Pyrazolin-5-ones 104B. 3-Pyrazolin-5-ones 10513. Metallic and Non-metallic Complexes 105A. 2-Pyrazolin-5-ones 105B. 3-Pyrazolin-5-ones 10714. Miscellaneous Derivatives 108Chapter III. 2-Pyrazolin-4-ones IllChapter IV. 2-Pyrazolin-4,5-diones 114Chapter V. 3-Pyrazolidinones 115Chapter VI. 3,4-Pyrazolidinediones 120Chapter VII. 3,5-Pyrazolidinediones1. Introduction 1232. Alkyl, Aralkyl, Heterocyclicalkyl and Aryl Substituted Derivatives 1243. Hydroxy and Alkoxy Substituted Derivatives 1284. Amino and Azo Substituted Derivatives 1285. Halogen Substituted Derivatives 1296. Nitroso Substituted Derivatives 1297. C-Acyl Substituted Derivatives 1298. N-Acyl Substituted Derivatives 130Chapter Vlll. 5-Imino-3-pyrazolidinones1. Introduction 1312. Alkyl, Alicyclic, Aralkyl, Heterocyclicalkyl, Heterocyclic and Aryl Substituted Derivatives 1323. Functional Group Derivatives 137Chapter IX. Miscellaneous 3,5-Pyrazolidinediones and Analogs 139Part 2. ApplicationsChapter I. Medical 143Chapter II. Color Photography 148Chapter III. Textile and Fabric Dyes 152Chapter IV. Analytical Reagents 155Chapter V. Miscellaneous 157Appendix. Systematic Tables of Pyrazolones and their Derivatives 161References 483Index 525