After studying ring-chain tautomerism of keto ami des and related derivatives of functionalized carboxylic acids for more than ten years, the authors consider it useful to summarize available results on these prototropic equilibria. First attempts to systematize the material were published by Jones in 1963 (Chapter 1, ref. 11). Much, sometimes contradictory, experimental data were scattered about the literature at that time; spectroscopic methods, applied to this field during the last two decades, were needed to revise several previous concepts. In the following years special aspects of…mehr
After studying ring-chain tautomerism of keto ami des and related derivatives of functionalized carboxylic acids for more than ten years, the authors consider it useful to summarize available results on these prototropic equilibria. First attempts to systematize the material were published by Jones in 1963 (Chapter 1, ref. 11). Much, sometimes contradictory, experimental data were scattered about the literature at that time; spectroscopic methods, applied to this field during the last two decades, were needed to revise several previous concepts. In the following years special aspects of ring-chain tautomerism have been discussed occasionally, but no attempt was previously made to cover the whole field. This review is designed to provide a comprehensive compilation of ring-chain tautomerism with one exception: carbohydrates which have already been treated repeatedly, have been omitted. The book is based on a monograph published in Russian: R. E. Valters, Ring-Chain Isomerism in Organic Chemistry. Zinatne. Riga, 1978. There fore, the arrangement and development of the theme is due mainly to one of the authors (R.E.Y.). In the present work the literature has been covered until the end of 1982.
1. Introduction.- 1.1. Ring-Chain Isomeric Interconversions. General Considerations.- 1.2. Tautomerism or Isomerism? System Mobility and Equilibrium Position.- 1.3. Methods of Investigation of Ring-Chain Addition Tautomerism.- 1.3.1. Chemical Methods.- 1.3.2. Visible and UV Spectroscopy.- 1.3.3. IR Spectroscopy.- 1.3.4. Nuclear Magnetic Resonance.- 1.3.5. Mass Spectrometry.- 1.3.6. X-Ray Diffraction Analysis.- 1.3.7. Polarography.- 1.3.8. Other Physical Methods.- References.- 2. Intramolecular Reversible Addition Reactions to the C=O Group.- 2.1. Aldehydo and Keto-carboxylic Acids and Their Derivatives Modified at the Carboxylic Group.- 2.1.1. Aldehydo- and Keto-carboxylic Acids.- 2.1.2. Acyl Chlorides.- 2.1.3. Amides, Hydrazides, and Amidines.- 2.1.4. Esters.- 2.1.5. Mixed Anhydrides.- 2.2. Hydroxy Aldehydes and Ketones and Related Compounds.- 2.2.1. Derivatives Containing a Hydroxy Group at Carbon (C-OH).- 2.2.2. Derivatives Containing a Hydroxy Group at Nitrogen (N-OH).- 2.3. Amino Aldehydes and Ketones and Related Compounds.- 2.3.1. Covalent Hydration of Nitrogen-Containing Heterocycles.- 2.3.2. Derivatives Containing Amino Groups at sp3-, Aromatic, and sp2-Carbon Atoms.- 2.3.3. Urea and Thiourea Derivatives.- 2.3.4. Dithiocarbamates.- 2.3.5. Sulfonamides and Sulfinamides.- 2.3.6. Pyridones.- 2.3.7. 1,3-Diazaheterocycles.- 2.3.8. Triazenes.- 2.3.9. Miscellaneous.- 2.4. Intramolecular Migration of O-, N-, and S-Acyl Groups.- 2.5. Oxa-, Aza-, and Thiacyclols.- 2.6. Mercapto Aldehydes and Ketones and Related Compounds.- 2.7. Intramolecular Addition of C-H Groups.- References.- 3. Intramolecular Reversible Addition Reactions to the C=N Group.- 3.1. OH-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 3.1.1. N-(Hydroxyalkyl) and N-(hydroxyaryl) imines.- 3.1.2. N-Hydroxyalkylhydrazones.- 3.1.3. Hydroxyalkyl and Hydroxyiminoalkyl Nitrones.- 3.1.4. Imines, Hydrazones, and Oximes of Hydroxyaldehydes and Hydroxyketones.- 3.1.5. Imines of Ketocarboxylic Acids.- 3.1.6. Fused Systems.- 3.2. N-H-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 3.2.1. N-Aminoalkylimines.- 3.2.2. N-Aminoalkyl and N-Aminoacyl Hydrazones and Related Compounds.- 3.2.3. 2-Benzimidoyl-benzamides and -benzenesulfonamides.- 3.2.4. N-(2- and 3-Hydroxyiminoalkyl)nitrones.- 3.2.5. Fused Systems.- 3.3. S-H-Derivatives of Imines and Hydrazones.- 3.4. Miscellaneous.- References.- 4. Intramolecular Reversible Addition Reactions to Other Groups.- 4.1. Addition to the C?N Group.- 4.2. Addition to C=C and C?C Groups.- 4.3. Addition to the P=O Group.- 4.4. Addition to the P=N Group.- 4.5. Addition to the S=O Group.- 4.6. Addition to the Se=O Group.- 4.7. Addition to the I=O Group.- References.- 5. Generalizations Concerning the Influence of Structural and External Factors on the Relative Stability of Ring and Chain Isomers.- 5.1. Structural Influences.- 5.1.1. Electronic Effects of Substituents at Interacting Groups.- 5.1.2. Steric Effects of Substituents at Interacting Groups.- 5.1.3. Structure of the Connecting Link.- 5.1.4. Steric Effects of the Substituents at the Connecting Link.- 5.1.5. Intramolecular Hydrogen Bonds.- 5.2. Influence of External Factors.- References.
1. Introduction.- 1.1. Ring-Chain Isomeric Interconversions. General Considerations.- 1.2. Tautomerism or Isomerism? System Mobility and Equilibrium Position.- 1.3. Methods of Investigation of Ring-Chain Addition Tautomerism.- 1.3.1. Chemical Methods.- 1.3.2. Visible and UV Spectroscopy.- 1.3.3. IR Spectroscopy.- 1.3.4. Nuclear Magnetic Resonance.- 1.3.5. Mass Spectrometry.- 1.3.6. X-Ray Diffraction Analysis.- 1.3.7. Polarography.- 1.3.8. Other Physical Methods.- References.- 2. Intramolecular Reversible Addition Reactions to the C=O Group.- 2.1. Aldehydo and Keto-carboxylic Acids and Their Derivatives Modified at the Carboxylic Group.- 2.1.1. Aldehydo- and Keto-carboxylic Acids.- 2.1.2. Acyl Chlorides.- 2.1.3. Amides, Hydrazides, and Amidines.- 2.1.4. Esters.- 2.1.5. Mixed Anhydrides.- 2.2. Hydroxy Aldehydes and Ketones and Related Compounds.- 2.2.1. Derivatives Containing a Hydroxy Group at Carbon (C-OH).- 2.2.2. Derivatives Containing a Hydroxy Group at Nitrogen (N-OH).- 2.3. Amino Aldehydes and Ketones and Related Compounds.- 2.3.1. Covalent Hydration of Nitrogen-Containing Heterocycles.- 2.3.2. Derivatives Containing Amino Groups at sp3-, Aromatic, and sp2-Carbon Atoms.- 2.3.3. Urea and Thiourea Derivatives.- 2.3.4. Dithiocarbamates.- 2.3.5. Sulfonamides and Sulfinamides.- 2.3.6. Pyridones.- 2.3.7. 1,3-Diazaheterocycles.- 2.3.8. Triazenes.- 2.3.9. Miscellaneous.- 2.4. Intramolecular Migration of O-, N-, and S-Acyl Groups.- 2.5. Oxa-, Aza-, and Thiacyclols.- 2.6. Mercapto Aldehydes and Ketones and Related Compounds.- 2.7. Intramolecular Addition of C-H Groups.- References.- 3. Intramolecular Reversible Addition Reactions to the C=N Group.- 3.1. OH-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 3.1.1. N-(Hydroxyalkyl) and N-(hydroxyaryl) imines.- 3.1.2. N-Hydroxyalkylhydrazones.- 3.1.3. Hydroxyalkyl and Hydroxyiminoalkyl Nitrones.- 3.1.4. Imines, Hydrazones, and Oximes of Hydroxyaldehydes and Hydroxyketones.- 3.1.5. Imines of Ketocarboxylic Acids.- 3.1.6. Fused Systems.- 3.2. N-H-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 3.2.1. N-Aminoalkylimines.- 3.2.2. N-Aminoalkyl and N-Aminoacyl Hydrazones and Related Compounds.- 3.2.3. 2-Benzimidoyl-benzamides and -benzenesulfonamides.- 3.2.4. N-(2- and 3-Hydroxyiminoalkyl)nitrones.- 3.2.5. Fused Systems.- 3.3. S-H-Derivatives of Imines and Hydrazones.- 3.4. Miscellaneous.- References.- 4. Intramolecular Reversible Addition Reactions to Other Groups.- 4.1. Addition to the C?N Group.- 4.2. Addition to C=C and C?C Groups.- 4.3. Addition to the P=O Group.- 4.4. Addition to the P=N Group.- 4.5. Addition to the S=O Group.- 4.6. Addition to the Se=O Group.- 4.7. Addition to the I=O Group.- References.- 5. Generalizations Concerning the Influence of Structural and External Factors on the Relative Stability of Ring and Chain Isomers.- 5.1. Structural Influences.- 5.1.1. Electronic Effects of Substituents at Interacting Groups.- 5.1.2. Steric Effects of Substituents at Interacting Groups.- 5.1.3. Structure of the Connecting Link.- 5.1.4. Steric Effects of the Substituents at the Connecting Link.- 5.1.5. Intramolecular Hydrogen Bonds.- 5.2. Influence of External Factors.- References.
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