Overview

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.

Full Product Details

Author:   Raimonds Valters
Publisher:   Springer-Verlag New York Inc.
Imprint:   Springer-Verlag New York Inc.
Edition:   Softcover reprint of the original 1st ed. 1985
Dimensions:   Width: 15.20cm , Height: 1.60cm , Length: 22.90cm
Weight:   0.436kg
ISBN:  

9781468448856

ISBN 10:   1468448854
Pages:   278
Publication Date:   14 March 2012
Audience:   Professional and scholarly ,  Professional & Vocational
Format:   Paperback
Publisher's Status:   Active
Availability:   Manufactured on demand  
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Table of Contents

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.- 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.- 2.2. Hydroxy Aldehydes and Ketones and Related Compounds.- 2.3. Amino Aldehydes and Ketones and Related Compounds.- 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.- 3.2. N-H-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 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.- 5.2. Influence of External Factors.- References.

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