This book is a comprehensive and contemporary treatment of the chemistry of alkanes, alkenes, dienes, acetylenes and aromatics. It covers all major aspects of the chemistry involved in hydrocarbon transformations. Each chapter deals with a specific type of transformation and details all related fundamental chemistry, including reactivity, selectivity, stereochemical considerations, mechanistic factors and practical applications. Chemical formulas and flow sheets assist readers in understanding discussions.

Geoge A. Olah, PHD, is the 1994 Nobel Laureate in Chemistry, Founding Director of the Loker. Hydrocarbon Research Institute, and Distinguished Loker Chair Professor at the University of Southern California. A pioneer in the hypercarbon Chemistry field, Dr. Olah has published numerous papers, books, and monographs. G.K. Surya Prakash, PHD, is the George A, and Judith A. Olah Nobel Laureate chair Professor and the Director of the Loker Hydrocarbon Research Institute at the University of Southern California. Kenneth Wade, PHD, DSc, FRS, is an Emeritus Professor at the University of Durham, UK and a Senior fellow of the Loker Hydrocarbon Research Institute at the University of Southern California. rpd Molnr, DSc, is an Emeritus Professor at the University of Szissed Hungary and a Senior Fellow of the Loker Hydrocarbon Research Institute at the University of Southern California. Robert E. Williams, Ph.d, is a Senior Fellow of the Loker Hydrocarbon Research Institute at the University of Southern California.

Foreword to the First Edition	p. xiii
Preface to the Second Edition	p. xv
Preface to the First Edition	p. xvii
Introduction: General Aspects	p. 1
Aims and Objectives	p. 1
Some Definitions	p. 2
Structures of Some Typical Hypercarbon Systems	p. 5
The Three-Center Bond Concept: Types of Three-Center Bonds	p. 10
The Bonding in More Highly Delocalized Systems	p. 21
Reactions Involving Hypercarbon Intermediates	p. 26
References	p. 31
Carbon-Bridged (Associated) Metal Alkyls	p. 37
Introduction	p. 37
Bridged Organoaluminum Compounds	p. 41
Beryllium and Magnesium Compounds	p. 50
Organolithium Compounds	p. 53
Organocopper, Silver, and Gold Compounds	p. 58
Scandium, Yttrium, and Lanthanide Compounds	p. 62
Titanium, Zirconium, and Hafnium Compounds	p. 64
Manganese Compounds	p. 66
Other Metal Compounds with Bridging Alkyl Groups	p. 68
Agostic Systems Containing Carbon-Hydrogen-Metal 3c-2e Bonds	p. 70
Conclusions	p. 76
References	p. 77
Carboranes and Metallacarboranes	p. 85
Introduction	p. 85
Carborane Structures and Skeletal Electron Numbers	p. 87
Closo Carboranes	p. 88
Nido and Arachno Carboranes	p. 89
Carbon Sites in Carboranes; Skeletal Connectivities k	p. 97
Skeletal Bond Orders in Boranes and Carboranes	p. 98
Localized Bond Schemes for Closo Boranes and Carboranes	p. 98
Lipscomb's Styx Rules and Williams' Six Rules	p. 98
Bond Orders and Skeletal Connectivities	p. 100
Bond Networks and Skeletal Connectivities	p. 101
Calculated Charge Distributions and Edge Bond Orders	p. 102
MO Treatments of Closo Boranes and Carboranes	p. 104
The Bonding in Nido and Arachno Carboranes	p. 107
Localized Bond Schemes	p. 107
MO Treatments of Nido and Arachno Boranes and Carboranes	p. 108
Some Boron-Free Nido and Arachno Systems	p. 110
Methods of Synthesis and Interconversion Reactions	p. 111
Some Carbon-Derivatized Carboranes	p. 114
Carboranyl C-H X Hydrogen-Bonded Systems	p. 114
Carboranyl-Metal Systems	p. 114
Some Aryl-Carboranes	p. 116
Boron-Derivatized Carboranes: Weakly Basic Anions [CB11H6X6]	p. 122
Metallacarboranes	p. 123
Structural Types, Electron Counts, and Isolobal Units	p. 123
Predicting Structures from Formulae	p. 126
Metal Complexes of CxBy Ring Systems	p. 130
Supraicosahedral Carborane Systems	p. 133
Conclusions	p. 137
References	p. 137
Mixed Metal-Carbon Clusters and Metal Carbides	p. 149
Introduction	p. 149
Complexes of CnHn Ring Systems with a Metal Atom: Nido-Shaped MCn Clusters	p. 150
Metal Complexes of Acyclic Unsaturated Ligands, CnHn+2	p. 157
Complexes of Unsaturated Organic Ligands with Two or More Metal Atoms: Mixed Metal-Carbon Clusters	p. 160
Metal Clusters Incorporating Core Hypercarbon Atoms	p. 162
Bulk Metal Carbides	p. 173
Metallated Carbocations	p. 176
Conclusions	p. 176
References	p. 177
Hypercoordinate Carbocations and Their Borane Analogs	p. 185
General Concept of Carbocations: Carbenium Versus Carbonium Ions	p. 185
Trivalent-Tricoordinate (Classical) Carbenium Ions	p. 186
Hypercoordinate (Nonclassical) Carbonium Ions	p. 187
Methods of Generating Hypercoordinate Carbocations	p. 188
Methods Used to Study Hypercoordinate Carbocations	p. 189
Nmr Spectroscopy in Solution	p. 189
13C NMR Chemical Shift Additivity	p. 192
Isotopic Perturbation Method	p. 192
Solid-State 13CNMRat Extremely Low Temperature	p. 193
X-Ray Diffraction	p. 193
Tool of Increasing Electron Demand	p. 194
Esca	p. 194
Low Temperature Solution Calorimetry	p. 195
Quantum Mechanical Calculations	p. 195
Methonium Ion (CH5+) and Its Analogs	p. 195
Alkonium Ions Incorporating Bridging Hydrogens (Protonated Alkanes, Cn H2n+3+)	p. 195
The Methonium Ion (CH5+)	p. 196
Multiply-Protonated Methane Ions and their Analogs	p. 202
Varied Methane Cations	p. 205
Ethonium Ion (C2H7+) and Analogs	p. 208
Proponium Ions and Analogs	p. 210
Higher Alkonium Ions	p. 211
Adamantonium Ions	p. 217
Hydrogen-Bridged Cycloalkonium Ions	p. 217
Hydrogen-Bridged Acyclic Ions	p. 221
Five-Center, Four-Electron Bonding Structures	p. 223
Hypercoordinate Carbocations Containing 3c-2e C C C Bonds	p. 223
Cyclopropylmethyl and Cyclobutyl Cations	p. 223
The 2-Norbornyl Cation	p. 229
The 7-Norbornyl Cation	p. 243
The 2-Bicyclo[2.1.1]hexyl Cation	p. 243
The Polymethyl 2-Adamantyl Cations	p. 245
Homoaromatic Cations	p. 247
Monohomoaromatic Cations	p. 247
Bishomoaromatic Cations	p. 249
Trishomoaromatic Cations	p. 256
Three-Dimensional Homoaromaticity	p. 258
Möbius Homoaromaticity	p. 259
Hypercoordinate (Nonclassical) Pyramidal Carbocations	p. 260
(CH)5+-Type Cations	p. 260
(CH)62+-Type Dications	p. 264
Hypercoordinate Heterocations	p. 266
Introduction	p. 266
Hydrogen-Bridged Silyl Cations	p. 266
Homoaromatic Heterocations	p. 267
Carbocation-Borane Analogs	p. 268
Introduction	p. 268
Hypercoordinate Methonium and Boronium Ions	p. 272
Cage Systems	p. 272
Hypercoordinate Onium-Carbonium Dications and Isoelectronic Onium-Boronium Cations	p. 274
Conclusions	p. 276
References	p. 277
Reactions Involving Hypercarbon Intermediates	p. 295
Introduction	p. 295
Reactions of Electrophiles with C-H and C-C Single Bonds	p. 298
Acid-Catalyzed Reactions and Rearrangements of Alkanes, Cycloalkanes, and Related Compounds	p. 298
Carbon-Hydrogen and Carbon-Carbon Bond Protolysis	p. 298
Isomerization and Rearrangement	p. 307
Alkylation	p. 320
Nitration and Nitrosation	p. 325
Halogenation	p. 328
Carbonylation	p. 331
Oxyfunctionalization	p. 332
Oxygenation with Hydrogen Peroxide	p. 332
Oxygenation with Ozone	p. 334
Oxygenation with Other Reagents	p. 337
Sulfuration	p. 339
Reactions of Coordinatively Unsaturated Metal Compounds and Fragments with C-H and C-C Ã Bonds	p. 340
Carbon-Hydrogen Bond Insertion	p. 342
Carbon-Carbon Bond Insertion	p. 362
Reactions of Singlet Carbenes, Nitrenes, and Heavy Carbene Analogs with C-H and C-C Bonds	p. 371
Rearrangement to Electron-Deficient Metal, Nitrogen, and Oxygen Centers	p. 377
Isomerization, Rearrangement, andRedistribution of Alkylmetal Compounds	p. 377
Rearrangements to Electron-Deficient Nitrogen and Oxygen Centers	p. 381
Electrophilic Reactions of À -Donor Systems	p. 383
Bridging Hypercoordinate Species with Donor Atom Participation	p. 388
Carbocations with 3c-2e Bond	p. 388
Five-Coordinate SN2 Reaction Transition States and Claimed Intermediates	p. 389
Six-Coordinate Hypervalent Compounds	p. 393
Conclusions	p. 394
References	p. 394
Conclusions and Outlook	p. 417
Index	p. 419
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