Chemistry of alicyclic compounds : structure and chemical transformations
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Bibliographic Information
Chemistry of alicyclic compounds : structure and chemical transformations
（Studies in organic chemistry, 38）
Elsevier , Elsevier Science Pub. Co. [distributor], 1989
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Includes bibliographies and index
Description and Table of Contents
Description
This book is designed to give an illustrative rather than an encyclopaedic view of the fascinating world of alicyclic compounds. It is focused on the basic topics of structure and chemical transformations. The classification and structural description of alicyclic compounds and an assessment of their stability is followed by the treatment of processes characterizing their dynamic behaviour. Further chapters describe useful methods for the synthesis of alicyclics by ring contraction, ring enlargement and transannular cyclization. Finally, the application of alicyclics for the construction of important natural products or interesting model compounds is discussed. The extensive bibliography of more than 1500 references and detailed subject index will be particularly useful. The book will be of interest to graduate students and lecturers in organic and physical organic chemistry, as well as to research chemists at universities and in the fine chemical, pharmaceutical and fragrance industries.
Table of Contents
1. Structural Foundations: Topology and Topography of Alicyclic Compunds. Systematics of alicyclic compounds. Chemical topology of the ring systems. Degree of saturation of alicyclic compounds. Configuration and conformation of the alicyclics. Topography of important alicyclic ring systems. References. 2. Structure-Energy Relations in Alicyclic Systems. Energy comparisons between ring systems. Stereostructure and energy content. Use of MO-theoretical methods. Force field calculations. Strain-reactivity relations. References. 3. Ring Transformations by Dynamic Processes. Intramolecular forms of motion. Conformational transformations. Configurational transformations. Reversible valence isomerizations. Dynamic behaviour and reactivity. References. 4. Preparation of Alicyclics by Ring Contraction. Ring contractions via cationic intermediates. Ring contractions via carbanions. Ring contractions via divalent carbon. Photochemical ring contractions. Thermal ring contractions. References. 5. Preparation of Alicyclics by Ring Enlargement. Ring enlargements via cationic intermediates. Ring enlargements via anionic intermediates, carbenes, and radicals. Ring enlargment by cleavage of primarily synthesized polycyclics. Sigmatropic rearrangements of cycloalkylvinyl compounds. References. 6. Transformation of Alicyclics by Transannular Reactions. Transannular ring closures via cationic intermediates (transannular p-cyclizations). Transannular ring closures via anionic intermediates and carbenes. Transannular ring closures via radical intermediates. Concerted transannular valence isomerizations. References. Subject Index
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