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Hypercarbon Chemistry

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Hypercarbon Chemistry HYPERCARBON CHEMISTRY HYPERCARBON CHEMISTRY Second Edition GEORGE A. OLAH G. K. SURYA PRAKASH KENNETH WADE ÁRPÁD MOLNÁR ROBERT E. WILLIAMS A JOHN WILEY & SONS, INC., PUBLICATION Copyright © 2011 by John Wiley & Sons, Inc. All rights reserved Published by John Wiley & Sons, Inc., Hoboken, New Jersey Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permissions. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifi cally disclaim any implied warranties of merchantability or fi tness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profi t or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data: Hypercarbon chemistry / by George A. Olah . [et al.]. – 2nd ed. p. cm. Includes index. ISBN 978-0-470-93568-2 (cloth) 1. Carbonium ions. 2. Organometallic chemistry. I. Olah, George A. (George Andrew), 1927- QD305.C3H97 2011 547.01–dc22 2010044306 Printed in the United States of America ePDF ISBN 9781118016442 ePub ISBN 9781118016459 oBook ISBN 9781118016466 10 9 8 7 6 5 4 3 2 1 In Memory of the Late Professor William N. Lipscomb CONTENTS Foreword to the First Edition xiii Preface to the Second Edition xv Preface to the First Edition xvii 1. Introduction: General Aspects 1 1.1. Aims and Objectives 1 1.2. Some Defi nitions 2 1.3. Structures of Some Typical Hypercarbon Systems 5 1.4. The Three-Center Bond Concept: Types of Three-Center Bonds 10 1.5. The Bonding in More Highly Delocalized Systems 21 1.6. Reactions Involving Hypercarbon Intermediates 26 References 31 2. Carbon-Bridged (Associated) Metal Alkyls 37 2.1. Introduction 37 2.2. Bridged Organoaluminum Compounds 41 2.3. Beryllium and Magnesium Compounds 50 2.4. Organolithium Compounds 53 2.5. Organocopper, Silver, and Gold Compounds 58 2.6. Scandium, Yttrium, and Lanthanide Compounds 62 2.7. Titanium, Zirconium, and Hafnium Compounds 64 2.8. Manganese Compounds 66 2.9. Other Metal Compounds with Bridging Alkyl Groups 68 vii viii CONTENTS 2.10. Agostic Systems Containing Carbon–Hydrogen–Metal 3c–2e Bonds 70 2.11. Conclusions 76 References 77 3. Carboranes and Metallacarboranes 85 3.1. Introduction 85 3.2. Carborane Structures and Skeletal Electron Numbers 87 3.2.1. Closo Carboranes 88 3.2.2. Nido and Arachno Carboranes 89 3.2.3. Carbon Sites in Carboranes; Skeletal Connectivities k 97 3.2.4. Skeletal Bond Orders in Boranes and Carboranes 98 3.3. Localized Bond Schemes for Closo Boranes and Carboranes 98 3.3.1. Lipscomb’s Styx Rules and Williams’ Stx Rules 98 3.3.2. Bond Orders and Skeletal Connectivities 100 3.3.3. Bond Networks and Skeletal Connectivities 101 3.3.4. Calculated Charge Distributions and Edge Bond Orders 102 3.4. MO Treatments of Closo Boranes and Carboranes 104 3.5. The Bonding in Nido and Arachno Carboranes 107 3.5.1. Localized Bond Schemes 107 3.5.2. MO Treatments of Nido and Arachno Boranes and Carboranes 108 3.5.3. Some Boron-Free Nido and Arachno Systems 110 3.6. Methods of Synthesis and Interconversion Reactions 111 3.7. Some Carbon-Derivatized Carboranes 114 3.7.1. Carboranyl C–H---X Hydrogen-Bonded Systems 114 3.7.2. Carboranyl–Metal Systems 114 3.7.3. Some Aryl-Carboranes 116 3.8. Boron-Derivatized Carboranes: Weakly Basic Anions − [CB11H6X6] 122 3.9. Metallacarboranes 123 3.9.1. Structural Types, Electron Counts, and Isolobal Units 123 3.9.2. Predicting Structures from Formulae 126 3.9.3. Metal Complexes of CxBy Ring Systems 130 3.10. Supraicosahedral Carborane Systems 133 3.11. Conclusions 137 References 137 4. Mixed Metal–Carbon Clusters and Metal Carbides 149 4.1. Introduction 149 4.2. Complexes of CnHn Ring Systems with a Metal Atom: Nido-Shaped MCn Clusters 150 4.3. Metal Complexes of Acyclic Unsaturated Ligands, CnHn+2 157 CONTENTS ix 4.4. Complexes of Unsaturated Organic Ligands with Two or More Metal Atoms: Mixed Metal–Carbon Clusters 160 4.5. Metal Clusters Incorporating Core Hypercarbon Atoms 162 4.6. Bulk Metal Carbides 173 4.7. Metallated Carbocations 176 4.8. Conclusions 176 References 177 5. Hypercoordinate Carbocations and Their Borane Analogs 185 5.1. General Concept of Carbocations: Carbenium Versus Carbonium Ions 185 5.1.1. Trivalent–Tricoordinate (Classical) Carbenium Ions 186 5.1.2. Hypercoordinate (Nonclassical) Carbonium Ions 187 5.2. Methods of Generating Hypercoordinate Carbocations 188 5.3. Methods Used to Study Hypercoordinate Carbocations 189 5.3.1. NMR Spectroscopy in Solution 189 5.3.2. 13C NMR Chemical Shift Additivity 192 5.3.3. Isotopic Perturbation Method 192 5.3.4. Solid-State 13C NMR at Extremely Low Temperature 193 5.3.5. X-Ray Diffraction 193 5.3.6. Tool of Increasing Electron Demand 194 5.3.7. ESCA 194 5.3.8. Low Temperature Solution Calorimetry 195 5.3.9. Quantum Mechanical Calculations 195 + 5.4. Methonium Ion (CH5 ) and Its Analogs 195 5.4.1. Alkonium Ions Incorporating Bridging Hydrogens + (Protonated Alkanes, CnH2n+3 ) 195 + 5.4.1.1. The Methonium Ion (CH5 ) 196 5.4.1.2. Multiply-Protonated Methane Ions and their Analogs 202 5.4.1.3. Varied Methane Cations 205 + 5.4.1.4. Ethonium Ion (C2H7 ) and Analogs 208 5.4.1.5. Proponium Ions and Analogs 210 5.4.1.6. Higher Alkonium Ions 211 5.4.1.7. Adamantonium Ions 217 5.4.1.8. Hydrogen-Bridged Cycloalkonium Ions 217 5.4.1.9. Hydrogen-Bridged Acyclic Ions 221 5.4.1.10. Five-Center, Four-Electron Bonding Structures 223 5.4.2. Hypercoordinate Carbocations Containing 3c–2e C---C---C Bonds 223 5.4.2.1. Cyclopropylmethyl and Cyclobutyl Cations 223 5.4.2.2. The 2-Norbornyl Cation 229 5.4.2.3. The 7-Norbornyl Cation 243 5.4.2.4. The 2-Bicyclo[2.1.1]hexyl Cation 243 5.4.2.5. The Polymethyl 2-Adamantyl Cations 245 x CONTENTS 5.5. Homoaromatic Cations 247 5.5.1. Monohomoaromatic Cations 247 5.5.2. Bishomoaromatic Cations 249 5.5.3. Trishomoaromatic Cations 256 5.5.4. Three-Dimensional Homoaromaticity 258 5.5.5. Möbius Homoaromaticity 259 5.6. Hypercoordinate (Nonclassical) Pyramidal Carbocations 260 + 5.6.1. (CH)5 -Type Cations 260 2+ 5.6.2. (CH)6 -Type Dications 264 5.7. Hypercoordinate Heterocations 266 5.7.1. Introduction 266 5.7.2. Hydrogen-Bridged Silyl Cations 266 5.7.3. Homoaromatic Heterocations 267 5.8. Carbocation–Borane Analogs 268 5.8.1. Introduction 268 5.8.2. Hypercoordinate Methonium and Boronium Ions 272 5.8.3. Cage Systems 272 5.8.4. Hypercoordinate Onium–Carbonium Dications and Isoelectronic Onium–Boronium Cations 274 5.9. Conclusions 276 References 277 6. Reactions Involving Hypercarbon Intermediates 295 6.1. Introduction 295 6.2. Reactions of Electrophiles with C–H and C–C Single Bonds 298 6.2.1. Acid-Catalyzed Reactions and Rearrangements of Alkanes, Cycloalkanes, and Related Compounds 298 6.2.1.1. Carbon–Hydrogen and Carbon–Carbon Bond Protolysis 298 6.2.1.2. Isomerization and Rearrangement 307 6.2.1.3. Alkylation 320 6.2.2. Nitration and Nitrosation 325 6.2.3. Halogenation 328 6.2.4. Carbonylation 331 6.2.5. Oxyfunctionalization 332 6.2.5.1. Oxygenation with Hydrogen Peroxide 332 6.2.5.2. Oxygenation with Ozone 334 6.2.5.3. Oxygenation with Other Reagents 337 6.2.6. Sulfuration 339 6.2.7. Reactions of Coordinatively Unsaturated Metal Compounds and Fragments with C–H and C–C σ Bonds 340 CONTENTS xi 6.2.7.1. Carbon–Hydrogen Bond Insertion 342 6.2.7.2. Carbon–Carbon Bond Insertion 362 6.2.8. Reactions of Singlet Carbenes, Nitrenes, and Heavy Carbene Analogs with C–H and C–C Bonds 371 6.2.9. Rearrangement to Electron-Defi cient Metal, Nitrogen, and Oxygen Centers 377 6.2.9.1. Isomerization, Rearrangement, and Redistribution of Alkylmetal Compounds 377 6.2.9.2.
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