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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