Organic Chemistry, Volume 2: Bridged Aromatic Compounds covers the research studies on cyclophane chemistry, bridged ferrocenes, and other similar compounds. This volume contains 10 chapters. The first five chapters describe the nomenclature, synthesis, reactions, chemistry, and dissymmetry of bridged aromatic compounds. The subsequent four chapters discuss the application of selected analytical methods to delineate the chemistry of these compounds, including UV and infrared absorption spectroscopy, X-ray methods, and nuclear and electron magnetic resonance. The last chapter provides tabulations of the more common physical properties reported for bridged aromatic compounds. Organic chemists and researchers and undergraduate and graduate organic chemistry students will greatly appreciate this book.
Inhalt
Preface
Acknowledgments
Nomenclature
Polymethylene or Disubstituted Aromatic System
Phenylene System
Benzo System
Ansa System
Bicyclo System
Cyclophane System
A New System
Preparation
The Acyloin Cyclization Method
The Friedel-Crafts Cyclization Method
The Halo-Amine Cyclization Method
The Halo-Ether Cyclization Method
The Wurtz Reaction
The Ziegler Cyclization Method
Cyclization by Pyrolysis of Acids and Their Salts
Pyrolysis of Hydrocarbons
The Hofmann Elimination Reaction Method
Cyclization by Pyrolysis of Other Compounds
The Ring-Contraction Method
Cyclization by Oxidative Coupling
Nonaromatic Routes to Bridged Aromatics
The Depolymerization Cyclization Method
The Dieckmann Cyclization Method
Cyclization by Amide Formation
Cyclization by Imine Formation
Miscellaneous Methods of Preparing Cyclophanes
Porphyrins and Related Compounds Containing Bridged Aromatic Nuclei
Natural Products Containing Cyclophane Links
References
Chemistry of the Bridged Nucleus
Carbon-Hydrogen Substituents
Halogen and Halogen-Containing Substituents
Oxygen-Containing Substituents
Nitrogen-Containing Substituents
Sulfur-Containing Substituents
Rearrangement of Cyclophane Bridges
Hydrogenation of the Aromatic Nucleus
Molecular Complexes of the Cyclophanes
Inclusion Compounds of the Cyclophanes
Photochemical Studies
Dehydrogenation of Cyclophanes to Polycyclics
Diels-Alder Reactions
References
Chemistry of the Bridge
Carbon-Hydrogen Substituents
Oxygen-Containing Substituents
Halogen Substituents
Nitrogen and Sulfur Substituents
Methylene Acidity
Bridgehead Oxidations
References
Dissymmetry of the Bridged Aromatics
Text
References
Ultraviolet Absorption Spectroscopy
Text
References
Infrared Absorption Spectroscopy
Text
References
X-Ray and Other Structural Studies
Text
References
Nuclear and Electron Magnetic Resonance Studies
Nuclear Magnetic Resonance
Electron Paramagnetic Resonance
References
Tables of Compounds
Tables
References
Author Index
Subject Index