NOMENCLATURE 1
Polymethylene or Disubstituted Aromatic System 2
Phenylene System 3
Benzo system 4
Ansa System 5
Bicyclo System 5
Cyclophane System 6
A New System 8
PREPARATION 24
The Acyloin Cyclization Method 27
The Friedel-Crafts Cyclization Method 43
The Halo-Amine Cyclization Method 66
The Halo-Ether Cyclization Method 75
The wurtz Reaction 88
The Ziegler Cyclization Method 96
Cyclization by Pyrolysis of Acids and Their Salts 100
Pyrolysis of Hydrocarbons 105
The Hofmann Elimination Reaction Method 106
Cyclization by Pyrolysis of Other Compounds 112
The Ring-Contraction Method 114
Cyclization by Oxidative Coupling 115
Nonaromatic Routes to Bridged Aromatics 121
The Depolymerization Cyclization Method 131
The Dieckmann Cyclization Method 133
Cyclization by Amide Formation 136
Cyclization by Imine Formation 142
Miscellaneous Methods of Preparing Cyclophanes 147
Porphyrins and Related Compounds Containing Bridged Aromatic Nuclei 176
Natural Products Containing Cyclophane Links 178
References 185
CHEMISTRY OF THE BRIDGED NUCLEUS 201
Carbon-Hydrogen Substituents 202
Halogen and Halogen-Containing Substituents 208
Oxygen-Containing Substituents 213
Nitrogen-Containing Substituents 236
Sulfur-Containing Substituents 244
Rearrangement of Cyclophane Bridges 245
Hydrogenation of the Aromatic Nucleus 247
Molecular Complexes of the Cyclophanes 249
Inclusion Compounds of the Cyclophanes 256
Photochemical Studies 258
Dehydrogenation of Cyclophanes to Polycyclics 259
Diels-Alder Reactions 260
References 262
CHEMISTRY OF THE BRIDGE 267
Carbon-Hydrogen Substituents 267
Oxygen-Containing Substituents 282
Halogen Substituents 316
Nitrogen and Sulfur Substituents 320
Methylene Acidity 324
Bridgehead Oxidations 324
References 326
DISSYMMETRY OF THE BRIDGED AROMATICS 333
Text 333
References 357
ULTRAVIOLET ABSORPTION SPECTROSCOPY 359
Text 359
References 382
INFRARED ABSORPTION SPECTROSCOPY 385
Text 385
References 392
χ-RAY AND OTHER STRUCTURAL STUDIES 393
Text 393
References 406
NUCLEAR AND ELECTRON MAGNETIC RESONANCE STUDIES 407
Nuclear Magnetic Resonance 407
Electron Paramagnetic Resonance 419
References 421
TABLES OF COMPOUNDS 423
Tables 424
References 495
Author Index 503
Subject Index 525