Handbook of Metathesis, 3 Volume Set

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ISBN: 9783527306169 | 3527306161
Cover: Hardcover
Copyright: 10/17/2003

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There is probably no name more closely linked to metathesis than that of Robert H. Grubbs of the California Institute of Technology. His pioneering work has led to the success of this important and fascinating reaction and in this comprehensive three-volume work he presents all its important aspects. The standard work on the topic The team of authors reads like a "Who's who" of metathesis Clearly divided into catalyst developments, organic synthesis applications and polymer synthesis A must-have for every organic and polymer chemist

Preface

xxi

References

xxv

List of Contributors

xxvii

Introduction

(3)

Robert H. Grubbs

References

(1)

The Role of the ``Tebbe Complex'' in Olefin Metathesis

(4)

Robert H. Grubbs

References

(2)

The Discovery and Development of High Oxidation State Mo and W Imido Alkylidene Complexes for Alkene Metathesis

(25)

Richard R. Schrock

Introduction

(1)

Tantalum Alkylidene Complexes

(4)

Early Tungsten Alkylidene Complexes

(2)

Development of Imido Alkylidene Complexes

(5)

Rhenium Alkylidene Complexes

(1)

Details of Reactions of Imido Alkylidene Complexes and Theoretical Calculations

(3)

Catalyst and Reaction Variations

(4)

Concluding Remarks

(5)

Acknowledgments

(1)

References

(4)

From III-Defined to Well-Defined W Alkylidene Complexes

(14)

Christophe Coperet

Frederic Lefebvre

Jean-Marie Basset

Introduction

(1)

Oxoalkylidene W Complexes

(2)

Alkoxy-Alkylidene W Complexes: Kress-Osborn System

(2)

Aryloxy-Alkylidene W Complexes: Leconte-Basset System

(1)

Amidoalkylidene W Complexes

(4)

Imido-Alkylidene W Complexes: Schrock's System

(2)

Summary and Outlooks

(3)

References

(2)

Fischer Metal Carbenes and Olefin Metathesis

(14)

Thomas J. Katz

Fischer Metal Carbenes and Olefin Metathesis

(1)

The Role of Fischer Metal Carbenes in Metathesis

(2)

Induction of Olefin Metatheses by Fischer Metal Carbenes

(4)

Properties of 2

(1)

Olefin Metatheses Initiated by Metal Carbene 1

(2)

Mechanistic Implications

(1)

Metatheses Initiated by Metal Carbene 2

(1)

Initiation of Acetylene Polymerization by Fischer Metal Carbenes

(2)

Introduction

(1)

Examples of Acetylene Polymerizations Initiated by Fischer Metal Carbenes

(1)

Actuation of Olefin Metathesis by Acetylenes

(6)

Metatheses of Cyclic and Acyclic Alkenes Actuated by An Acetylene

(1)

Reaction of Enynes With Fischer Metal Carbenes

(1)

Rearrangement of Enynes to Dienes

(1)

References

(4)

The Discovery and Development of Well-Defined, Ruthenium-Based Olefin Metathesis Catalysts

(25)

SonBinh T. Nguyen

Tina M. Trnka

The Discovery of Well-Defined Ruthenium Olefin Metathesis Catalysts: A Personal Account

(4)

SonBinh Nguyen

(PPh3)2 Cl2 Ru=CH-CH=CPh2, the First Well-Defined, Metathesis-Active Ruthenium Alkylidene Complex

(1)

(PCy3)2 Cl2 Ru=CH-CH=CPh2, A Well-Defined Ruthenium Alkylidene Catalyst for the Metathesis of Acyclic Olefins

(1)

Initial Applications of Olefin Metathesis Chemistry Catalyzed by (PCy3)2 Cl2 Ru=CH-CH=CPh2

(1)

More Accessible Ruthenium Alkylidene Sources

(3)

2nd-Generation Grubbs Catalysts

(5)

N-Heterocyclic Carbene (NHC) Ligands

(3)

Multi-Component Ruthenium-Based Olefin Metathesis Catalyst Systems and Homogeneous Catalyst Precursors

(1)

Solid-Supported Ruthenium-Based Olefin Metathesis Catalysts

(6)

Conclusions

(6)

References

(5)

Synthesis of Ruthenium Carbene Complexes

(9)

Warren R. Roper

Introduction

(1)

The First Ruthenium Carbene Complexes

(2)

Ruthenium Methylene Complexes

(4)

Ruthenium Dihalocarbene Complexes

(3)

Acknowledgments

(1)

References

(2)

Synthesis of Rhodium and Ruthenium Carbene Complexes with a 16-Electron Count

(17)

Helmut Werner

Justin Wolf

Introduction

(1)

Rhodium(I) Carbenes from Diazoalkanes

(3)

Ruthenium(II) Carbenes and Vinylidenes from Terminal Alkynes

(10)

Conclusions

108

(4)

Acknowledgements

109

(1)

References

109

(3)

Mechanism of Ruthenium-Catalyzed Olefin Metathesis Reactions

112

(20)

Melanie S. Sanford

Jennifer A. Love

Introduction

112

(1)

First-Generation Bis-Phosphine Catalyst Systems

112

(11)

General Mechanistic Considerations

112

(4)

Substituent Effects in Ruthenium-Catalyzed Olefin Metathesis

116

(2)

Thermal Decomposition of Ruthenium Catalysts

118

(2)

Decomposition in the Presence of Functional Groups

120

(1)

Mechanistic Considerations in Other First-Generation Ruthenium Metathesis Catalysts

120

(3)

Second-Generation Ruthenium Olefin Metathesis Catalysts

123

(6)

General Mechanistic Considerations

124

(1)

Substituent Effects in Ruthenium-Catalyzed Olefin Metathesis

125

(2)

Thermal Decomposition of Ruthenium Catalysts

127

(1)

Decomposition in the Presence of Functional Groups

127

(1)

Other Second-Generation Ruthenium Catalysts

128

(1)

Conclusions

129

(3)

References

130

(2)

Intrinsic Reactivity of Ruthenium Carbenes

132

(41)

Christian Adlhart

Peter Chen

Introduction

132

(3)

Electrospray Ionization Mass Spectrometry (ESI MS) of Transition Metal Complexes

135

(4)

Electrospray Ionization

135

(1)

Tandem Mass Spectrometry

136

(1)

Reaction Conditions in the Collision Cell of the Tandem ESI MS

137

(2)

General Reactivity of Ruthenium Carbene Complexes in the Gas Phase

139

(8)

Dissociative Mechanism

139

(2)

Evidence for ROMP and RCM

141

(2)

Systematic Variation of a Common Structural Motif -- Steric Effects and Halogen Effects

143

(3)

Conclusions

146

(1)

Three Key Factors that Determine the Activity of Metathesis Catalysts

147

(20)

Solution-Phase Pre-Equilibria: Activation

147

(1)

Pre-Equilibria During the Turnover: Backbiting

148

(7)

Catalyst Commitment: Potential Surface

155

(12)

Conclusions

167

(6)

Compound Numbers

167

(2)

References

169

(4)

The Discovery and Development of High Oxidation State Alkylidyne Complexes for Alkyne Metathesis

173

(17)

Richard R. Schrock

Introduction

173

(1)

Alkylidyne Complexes of Tantalum

174

(1)

Alkylidyne Complexes of Tungsten

174

(4)

Formation of Trialkoxy Alkylidyne Complexes from W2(OR)6 Species

178

(2)

Alkylidyne Complexes of Molybdenum

180

(1)

Reactions that Limit Metathesis Activity

181

(4)

Alkylidyne Complexes of Rhenium

185

(1)

Conclusions and Comments

186

(4)

Acknowledgments

187

(1)

References

187

(3)

Well-Defined Metallocarbenes and Metallocarbynes Supported on Oxide Supports Prepared via Surface Organometallic Chemistry: A Source of Highly Active Alkane, Alkene, and Alkyne Metathesis Catalysts

190

(1)

Christophe Coperet

Frederic Lefebvre

Jean-Marie Basset

Introduction

190

(1)

Preparation and Characterization of Well-Defined Metallocarbenes and Metallocarbynes via Surface Organometallic Chemistry

191

(4)

Strategy and Tools in Surface Organometallic Chemistry

191

(1)

Application to the Preparation of Well-Defined Metallocarbene and Metallocarbyne Supported on Oxides

192

(3)

Reactivity in Alkene and Alkyne Metathesis

195

(5)

Group 5 and 6 Metallocarbenes and Metallocarbynes Supported on Oxides

195

(2)

Group 7 Metallocarbenes and Metallocarbynes Supported on Oxides

197

(3)

Reactivity in Alkane Metathesis

200

(1)

Summary and Outlook

201

(1)

Acknowledgments

202

(1)

References

202

List of Contributors

xxi

Olefin Metathesis and Related Reactions in Organic Synthesis: Introduction to Metal-Carbon Double Bonds in Organic Synthesis

(4)

Robert H. Grubbs

References

(1)

General Ring-Closing Metathesis

(123)

So-Yeop Han

Sukbok Chang

Introduction

(2)

Synthesis of Carbocyles

(17)

Carbocyclization

(9)

Medium-Sized Carbocycles

(6)

Spiro Carbocycles

(2)

Synthesis of Bridged Bicycloalkenes

(5)

Synthesis of Heterocycles Containing Si, P, S, or B

(9)

Si-Heterocycles

(3)

P-Heterocycles

(3)

S-Heterocycles

(2)

B-Heterocycles

(1)

Synthesis of Cyclic Ethers

(8)

Mono- and Bicyclic Ethers

(5)

Polycyclic Ethers

(3)

Applications to N-Heterocycles and Peptide Chemistry

(19)

N-Heterocycles

(6)

Small and Medium-Sized Lactams

(2)

Cyclic Amino Acids, Peptides, and Peptidomimetics

(11)

Synthesis of Macrocycles

(9)

Macrocycles

(2)

Macrolactones

(5)

Macrolactams

(1)

Synthesis of Cyclic Conjugated Dienes

(3)

Alkyne Metathesis

(3)

Enyne Metathesis

(6)

General Enyne Metathesis

(3)

Dienyne Metathesis

(3)

Multi-Directional RCM

(2)

Tandem Processes

(6)

Tandem ROM/RCM

(4)

Other Tandem RCM

(2)

Asymmetric RCM

(2)

Synthesis of Complex Molecules

(32)

Template-Directed RCM

(1)

RCM in Supramolecular Chemistry

(13)

Synthetic Applications

109

(10)

References

119

(9)

Catalytic Asymmetric Olefin Metathesis

128

(23)

Amir H. Hoveyda

Introduction

128

(1)

The Catalyst Construct

129

(1)

Mo-Catalyzed Kinetic Resolution With Hexafluoro-Mo Catalysts

129

(1)

Chiral Mo-Diolate Complexes for Kinetic Resolution and Asymmetric Synthesis

130

(15)

Chiral Biphen-Mo Catalysts

130

(1)

Catalytic Kinetic Resolution Through Mo-Catalyzed ARCM

130

(1)

Catalyst Modularity and Optimization of Mo-Catalyzed ARCM Efficiency and Selectivity

131

(2)

Catalytic Asymmetric Synthesis Through Mo-Catalyzed ARCM

133

(4)

Catalytic Asymmetric Synthesis Through Tandem Mo-Catalyzed AROM/RCM

137

(5)

Catalytic Asymmetric Synthesis Through Tandem Mo-Catalyzed AROM/CM

142

(1)

Towards User-Friendly and Practical Chiral Mo-Based Catalysts for Olefin Metathesis

143

(2)

Chiral Ru-Based Olefin Metathesis Catalysts

145

(2)

Conclusions and Outlook

147

(4)

Acknowledgments

148

(1)

References

148

(3)

Tandem Ring-Closing Metathesis

151

(25)

Stefan Randl

Siegfried Blechert

Introduction

151

(1)

Tandem Metathesis Involving Double Bonds Only

152

(12)

RRM of Alkenyl-Substituted Cycloolefins

152

(8)

RRM of bis Alkenyl-Substituted Cycloolefins

160

(4)

Tandem Reactions of Polycycloolefins

164

(1)

Tandem RCM Involving Enyne Reactions

164

(8)

Tandem Reactions with Triple Bonds As ``Relays''

164

(2)

Tandem Processes Involving Ring Rearrangement

166

(3)

Alkyne Trimerizations Catalyzed by Metathesis Catalysts

169

(2)

Other Tandem Processes Involving C--C Triple Bonds

171

(1)

Summary and Outlook

172

(4)

References

173

(3)

Ene-Yne Metathesis

176

(29)

Miwako Mori

Introduction

176

(4)

Transition Metal-Carbene Complex-Catalyzed Enyne Metathesis

180

(14)

Ring-Closing Metathesis (RCM) of Enyne Using Ruthenium Carbene Complex

180

(6)

Ring-Opening Metathesis--Ring-Closing Metathesis of Cycloalkene-Yneo

186

(2)

Intermolecular Enyne Metathesis (Cross-Metathesis)

188

(6)

Skeletal Reorganization Using Transition Metals

194

(4)

Utilization of Enyne Metathesis for the Synthesis of Natural Products and Related Biologically Active Substances

198

(2)

Perspective

200

(5)

References

203

(2)

Ring-Opening Cross-Metatheses

205

(33)

Thomas O. Schrader

Marc L. Snapper

Introduction

205

(1)

Early Examples of ROCM

206

(7)

Mechanistic Insight

206

(1)

Early Efforts toward a Selective ROCM

207

(2)

Well-Defined Metal Complexes as Catalysts

209

(3)

New Opportunities for Olefin Metathesis

212

(1)

Selective ROCM Reactions

213

(15)

ROCM Involving Cyclobutenes

213

(3)

Regio- and Stereoselective ROCM

216

(2)

ROCM of Bridged Bicyclic Alkenes

218

(5)

ROCM Reactions of Cyclopropenes

223

(1)

ROCM Reactions Involving Unstrained Cycloolefins

224

(1)

ROCM Reactions of Trisubstituted Olefins

224

(2)

Variations of ROCM

226

(1)

Ring Expansion via Olefin Metathesis

226

(2)

Enantioselective ROCM

228

(2)

Mo-Catalyzed Asymmetric ROCM

228

(2)

A Recyclable Chiral Ruthenium Catalyst for Asymmetric ROCM

230

(1)

ROCM in Total Synthesis

230

(3)

Conclusions

233

(5)

References

235

(3)

Ring-Expansion Metathesis Reactions

238

(8)

Choon Woo Lee

References

244

(2)

Olefin Cross-Metathesis

246

(50)

Arnab K. Chatterjee

Olefin Forming Cross-Coupling Reactions

246

(1)

Olefin Metathesis and Selectivity Problems in CM

247

(2)

Metathesis Catalyst Overview

249

(1)

Selectivity Challenges in CM

250

(2)

Stereoselective CM Reactions

252

(4)

Product-Selective Reactions by CM

256

(2)

Styrene CM Reactions

258

(3)

Trisubstituted Olefin Synthesis by CM

261

(3)

Electron-Poor Olefins in CM

264

(5)

Reagent Synthesis by CM

269

(6)

Applications of CM

275

(3)

Bioorganic Applications of CM

278

(10)

CM Product-Selectivity Model

288

(2)

Conclusions

290

(6)

References

292

(4)

Olefin Metathesis Strategies in the Synthesis of Biologically Relevant Molecules

296

(27)

Jennifer A. Love

Introduction

296

(2)

Olefin Metathesis Strategies in Complex Molecule Synthesis

296

(1)

Catalysts for Olefin Metathesis

297

(1)

RCM and ROM in Complex Molecule Synthesis

298

(14)

Laulimalide

298

(4)

Boronolide

302

(1)

Ingenol

303

(1)

Asteriscanolide

303

(2)

(+)-FR900482

305

(1)

Salicylihalamide

306

(1)

Roseophilin

307

(2)

Ircinal A and Manzamine A

309

(1)

Amphidinolide A

309

(1)

Peptidomimetics

310

(2)

Ring-Closing Ene-Yne Metathesis

312

(2)

Cross-Metathesis in the Synthesis of Complex Molecules

314

(2)

( -- )-Cylindrocyclophanes A and F

314

(1)

Garsubellin A

315

(1)

(+)-Brefeldin A

315

(1)

ROMP in Complex Molecule Synthesis

316

(2)

Conclusions

318

(5)

References

319

(4)

Vignette 1 The Olefin Metathesis Reaction in Complex Molecule Construction

323

(15)

K. C. Nicolaou

Scott A. Snyder

Acknowledgments

334

(1)

References

335

(3)

Vignette 2 Applications of Ring-Closing Metathesis to Alkaloid Synthesis

338

(15)

Stephen F. Martin

Introduction

338

(1)

Methodological Studies

339

(3)

Synthesis of Alkaloid Natural Products

342

(8)

Conclusions

350

(1)

Acknowledgments

351

(1)

References

351

(2)

Vignette 3 Radicicol and the Epothilones: Total Synthesis of Novel Anticancer Agents Using Ring-Closing Metathesis

353

(8)

Jon T. Njardarson

Robert M. Garbaccio

Samuel J. Danishefsky

References

359

(2)

The Use of Olefin Metathesis in Combinatorial Chemistry: Supported and Chromatography-Free Syntheses

361

(42)

Andrew M. Harned

Donald A. Probst

Paul R. Hanson

Introduction

361

(1)

Metathesis Reactions Toward Supported Synthesis and Library Generation

362

(13)

Ring-Closing Metathesis (RCM)

362

(7)

Cross-Metathesis (X-MET)

369

(6)

Polymer-Supported Metathesis Catalysts

375

(2)

ROMP-Based Strategies

377

(19)

ROMPgel Reagents

378

(8)

ROMP as a Purification Tool

386

(4)

ROMPspheres

390

(1)

ROM Polymers as Supports

391

(5)

Conclusions

396

(7)

Acknowledgements

399

(1)

References

399

(4)

Metal-Catalyzed Olefin Metathesis in Metal Coordination Spheres

403

(29)

Eike B. Bauer

J. A. Gladysz

Introduction

403

(1)

Earliest Literature

404

(1)

Ferrocenes

405

(5)

Sophisticated Target Molecules: Catenanes and Knots

410

(4)

Systematic Investigation of Reaction Scope

414

(6)

Additional Literature Examples

420

(5)

Towards Additional Types of Sophisticated Target Molecules

425

(4)

Summary

429

(1)

Addendum

429

(3)

Acknowledgments

429

(1)

References

430

(2)

Alkyne Metathesis

432

(31)

Alois Furstner

Introduction

432

(1)

Classical Catalyst Systems for Alkyne Metathesis

432

(2)

Recent Advances in Catalyst Design

434

(3)

Preparative Applications of Alkyne Metathesis

437

(21)

Alkyne Homometathesis Reactions

437

(2)

Alkyne Cross-Metathesis

439

(4)

Ring-Closing Alkyne Metathesis (RCAM)

443

(5)

Applications of RCAM to Natural Product Synthesis

448

(8)

Post-Metathesis Transformations Other Than Lindlar Hydrogenation: Selective Synthesis of (E)-Alkenes and Heterocyclic Motifs

456

(2)

Conclusions and Outlook

458

(5)

References

459

(4)

Metathesis of Silicon-Containing Olefins

463

(28)

Bogdan Marciniec

Cezary Pietraszuk

Introduction

463

(1)

Self-Metathesis of Alkenylsilanes

464

(1)

Cross-Metathesis vs. Silylative Coupling (Trans-Silylation) of Alkenes with Vinylsilanes

464

(6)

Cross-Metathesis of Allylsilanes with Alkenes

470

(2)

Ring-Closing Metathesis of Silicon-Containing Dienes

472

(4)

Ring-Opening Metathesis/Cross-Metathesis

476

(2)

Polycondensation vs. Ring Closing of Divinyl-Substituted Silicon Compounds

478

(3)

ADMET Polymerization of Silicon-Containing Dienes

481

(2)

Ring-Opening Metathesis Polymerization of Silacycloalkenes

483

(1)

Ring-Opening Metathesis Polymerization of Silyl-Substituted Cycloalkenes

483

(2)

Degradation vs. Functionalization of Polymers

485

(6)

References

486

(5)

Commercial Applications of Ruthenium Metathesis Processes

491

(1)

Richard L. Pederson

Introduction

491

(1)

Fine Chemicals

491

(4)

Agrochemicals: Insect Pheromones

492

(2)

Polymer Additives

494

(1)

Fuel Additives

494

(1)

Drug Discovery

494

(1)

Pharmaceutical Applications

495

(10)

Future Directions for Metathesis

505

(1)

Summary

506

(1)

References

507

List of Contributors

xxi

Introduction

(1)

Robert H. Grubbs

Living Ring-Opening Olefin Metathesis Polymerization

(70)

Grainne Black

Declan Maher

Wilhelm Risse

Historic Overview of Living Polymerization Systems

(2)

Definition of Living Polymerization and Relevant Terminology

(2)

Introduction to ROMP

(5)

Olefin Metathesis Catalysts for Living Polymerizations

(61)

Titanacyclobutane Compounds

(5)

Tantalum-Alkylidene and Tantalacyclobutane Complexes for Norbornene Polymerizations

(1)

Tungsten Catalysts

(4)

Imido Molybdenum-Alkylidene Complexes

(12)

Imido Tungsten- and Molybdenum-Alkylidene Catalysts for ROMP of Monomers Containing Cyclobutene, Bicyclooctadiene, and Bicyclooctadiene Ring Systems

(9)

Tungsten- and Molybdenum-Alkylidene Catalysts in Cyclopentene Polymerizations

(1)

Paracyclophene Polymerizations

(1)

Ruthenium Catalysts and Living ROMP

(19)

Star-Shaped Polymers via ROMP

(3)

References

(6)

Synthesis of Copolymers

(46)

Ezat Khosravi

Introduction

(1)

Random Copolymers

(4)

Block Copolymers

(16)

Sequential Addition of Monomers

(7)

Coupling Reaction

(1)

Transformation of Propagating Species

(6)

Application of Well-Defined Bimetallic Initiators

(2)

Comb and Graft Copolymer

(6)

Combination of ROMP and Anionic Polymerization

(2)

Combination of ROMP and ATRP

(1)

Combination of ROMP and Cationic Polymerization

(1)

Combination of ROMP and Wittig-Type Reaction

(1)

Repetitive ROMP

(2)

Multi-Shaped Copolymers

(5)

Alternating Copolymers

103

(2)

Cross-Linked Copolymers

105

(13)

Well-Defined, Cross-Linked System via Direct Copolymerization

105

(5)

Cross-Linked Systems via Homopolymerization of Monomers with Cross-Linkable Side Chains

110

(2)

Cross-Linked Material via Combination of ROMP and Oxidative Polymerization

112

(1)

References

113

(5)

Conjugated Polymers

118

(25)

W. James Feast

Introduction

118

(3)

Strategies for Applying ROMP in the Synthesis of Conjugated Polymers

121

(1)

Direct Routes from Monomer to Conjugated Polymer Via Chain-Growth Processes

122

(5)

Direct Routes from Monomer to Conjugated Polymer Via Step-Growth Processes

127

(2)

Indirect Routes to Conjugated Polymer Via Processable Precursor Polymers

129

(10)

Conclusions

139

(4)

References

139

(4)

Stereochemistry of Ring-Opening Metathesis Polymerization

143

(37)

James G. Hamilton

Introduction

143

(1)

Consequences of cis/trans Isomerism and Tacticity in ROMP Polymers

144

(2)

Determination of the Stereochemistry of ROMP Polymers

146

(10)

Cis/trans Double-Bond Ratio

146

(3)

Tacticity

149

(7)

Control and Interpretation of Stereochemistry

156

(24)

Ratio and Distribution of cis and trans Double Bonds

156

(13)

Tacticity

169

(7)

References

176

(4)

Syntheses and Applications of Bioactive Polymers Generated by Ring-Opening Metathesis Polymerization

180

(46)

Laura L. Kiessling

Robert M. Owen

Introduction

180

(3)

Synthesis of Biologically Active Polymeric Displays

183

(20)

Carbohydrate-Containing Polymeric Displays

183

(6)

Peptide-Substituted Polymers

189

(4)

Synthesis of DNA/Polymer Conjugates via ROMP

193

(2)

Synthesis of Drug/Polymer Conjugates via ROMP

195

(1)

Post-Polymerization Modification Strategies

196

(3)

End-Capping Strategies

199

(4)

Applications of Biologically Active Polymeric Displays

203

(17)

Protein-Carbohydrate Interactions

203

(8)

Integrins and Cellular Adhesion

211

(2)

Pathogenic Organisms

213

(3)

Cell Clustering

216

(1)

Bacterial Chemotaxis

216

(4)

Conclusions

220

(6)

References

222

(4)

Metathesis Polymerization: A Versatile Tool for the Synthesis of Surface-Functionalized Supports and Monolithic Materials

226

(29)

Michael R. Buchmeiser

Introduction

226

(1)

Precipitation Polymerization-Based Techniques

226

(4)

Grafting Techniques

230

(9)

Coating Techniques

239

(1)

Monolithic Supports

240

(11)

Basics and Concepts

241

(1)

Manufacture of Metathesis-Based Monolithic Supports

242

(1)

Microstructure of Metathesis-Based Rigid Rods

242

(3)

Functionalization, Metal Removal, and Metal Content

245

(2)

Applications of Functionalized Metathesis-Based Monoliths in Catalysis

247

(4)

Conclusions, Summary, and Outlook

251

(4)

Acknowledgments

251

(1)

References

251

(4)

Telechelic Polymers from Olefin Metathesis Methodologies

255

(28)

Christopher W. Bielawski

Marc A. Hillmyer

Introduction and Background

255

(3)

Telechelic Polymers from Metathesis Polymerizations

258

(5)

Molecular Weight and Functionality Control in a ROMP/CT System

260

(3)

Syntheses and Applications of Telechelic Polymers Prepared Using Metathesis

263

(16)

Synthesis of Telechelic Polymers Using Ill-Defined Catalysts

264

(3)

Synthesis of Telechelic Polymers Using Well-Defined Metal Alkylidenes

267

(10)

Synthesis of End-Functionalized Polymers Using Functionalized Initiators

277

(2)

Conclusions and Outlook

279

(4)

References

280

(3)

ADMET Polymerization

283

(71)

Stephen E. Lehman, Jr.

Kenneth B. Wagener

Introduction

283

(5)

ADMET: The Metathesis Polycondensation Reaction

288

(6)

Kinetics and Equilibrium Considerations

289

(2)

Molecular Weight Distribution

291

(1)

Interchange Reactions

291

(1)

Cyclization vs. Polymerization

292

(1)

Monomer Purity

293

(1)

Early Observations in the Evolution of ADMET Polymerization: Reactions of Non-Conjugated Dienes with Classical Metathesis Catalysts

294

(3)

ADMET of Non-Conjugated Hydrocarbon Dienes with Well-Defined Metathesis Catalysts

297

(13)

Linear Terminal Dienes

297

(3)

Branched Terminal Dienes

300

(5)

Geminal Disubstituted Olefins

305

(2)

1,2-Disubstituted Olefins

307

(1)

Trisubstituted Olefins

308

(2)

ADMET Copolymerization

310

(1)

Synthesis of Conjugated Polymers via ADMET

311

(5)

Polyacetylenes

311

(2)

Polyphenylenevinylenes

313

(2)

Other Conjugated Polymers

315

(1)

ADMET Polymerization of Functionalized Dienes

316

(13)

Ethers, Acetals, and Alcohols

318

(1)

Amines

319

(1)

Boronates

320

(1)

Thioethers

321

(1)

Carbonyl Compounds

322

(3)

Halides

325

(1)

Silicon Compounds

325

(4)

Organometallic Compounds

329

(1)

Retro-ADMET: Towards Recycling of Unsaturated Polymers with Well-Defined Metathesis Catalysts

329

(2)

Telechelic Oligomers via ADMET

331

(1)

Kinetics and Mechanism

332

(6)

Modeling Polyolefins with ADMET

338

(7)

Hydrogenation of ADMET Polymers

338

(1)

Branched Polyethylene

339

(3)

Functionalized Polyethylene

342

(3)

Towards Biologically Useful Polymers via ADMET

345

(2)

Solid-State Polymerization

347

(1)

Conclusions and Outlook

347

(7)

References

347

(7)

Acyclic Diyne Metathesis Utilizing in Situ Transition Metal Catalysts: An Efficient Access to Alkyne-Bridged Polymers

354

(21)

Uwe H. F. Bunz

Introduction

354

(3)

Alkyne Metathesis

355

(2)

ADIMET: Synthesis of Alkyne-Bridged Polymers

357

(13)

Synthesis of PPEs by in situ ADIMET

360

(3)

Synthesis of PPE-PPV Copolymers by in situ ADIMET

363

(2)

Synthesis of Other PAEs by ADIMET

365

(5)

Alkyne-Bridged Carbazole Polymers (PCE) by ADIMET

370

(1)

Conclusions

370

(5)

Acknowledgments

371

(1)

References

371

(4)

Polymerization of Substituted Acetylenes

375

(32)

Toshio Masuda

Fumio Sanda

Introduction

375

(3)

Polymerization Catalysts

378

(6)

Mo and W Catalysts

378

(3)

Nb and Ta Catalysts

381

(1)

Rh Catalysts

382

(2)

Other Group 8--10 Metal Catalysts

384

(1)

Controlled Polymerizations

384

(5)

Living Polymerization by Metal Halide-Based Metathesis Catalysts

385

(2)

Living Polymerization by Single-Component Metal-Carbene Catalysts

387

(1)

Stereospecific Living Polymerization by Rh Catalysts

388

(1)

New Monomers and Functional Polymers

389

(18)

Gas-Permeable Polyacetylenes

396

(1)

Optically Active Polyacetylenes

397

(2)

Other Functional Polyacetylenes

399

(2)

References

401

(6)

Commercial Applications of Ruthenium Olefin Metathesis Catalysts in Polymer Synthesis

407

(12)

Mark S. Trimmer

Introduction

407

(1)

Background

407

(1)

New Developments

408

(1)

Poly-DCPD

409

(2)

Other ROMP Polymers

411

(2)

Hydrogenated ROMP Polymers

413

(1)

Depolymerization

414

(1)

Summary

414

(5)

References

414

(5)

Index

419

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Handbook of Metathesis, 3 Volume Set

Summary

Author Biography

Table of Contents

Supplemental Materials