Pericyclic Reactions - A Textbook Reactions,

Based on twelve years of teaching a graduate course, this long awaited textbook presents Diels-Alder reactions, electrocyclic reactions, sigmatropic rearrangements plus many more topics in a highly didactic way. Throughout the focus is on the important facts and aspects, with both classical and new examples explained in detail.The only up-to-date work of its kind on the market, this is an invaluable tool for students and lecturers in chemistry, organic chemists, and libraries.With a foreword by Nobel Laureate Roald Hoffmann.

<b>S. Sankararaman</b> is Professor at the Indian Institute of Technology, Madras, India and his research interests are modern synthetic chemistry, electron transfer reactions and radical chemistry. He has authored several publications in renowned journals and is an Alexander-Von-Humboldt Fellow.

Foreword

v

Preface

xiii

Molecular Orbitals and Their Symmetry

1

(18)

Molecular Orbitals

1

(3)

Molecular Orbitals of Conjugated Polyene Systems

4

(2)

Symmetry Elements and Symmetry Operations

6

(1)

Definition and Classification of Pericyclic Reactions

6

(4)

Electrocyclic Ring Closure and Ring Opening Reactions

9

(1)

Cycloaddition and Cycloreversion Reactions

9

(1)

Sigmatropic Rearrangements

9

(1)

Chelotropic Reactions

9

(1)

Group Transfer Reactions

10

(1)

Methods of Analyzing Pericyclic Reactions

10

(9)

Orbital Symmetry Correlation Method

11

(2)

Frontier Orbital Method

13

(1)

Transition State Aromaticity Method

14

(3)

References

17

(2)

Electrocyclic Reactions

19

(63)

Definition of Electrocyclic Reactions

19

(1)

Classification of Electrocyclic Reactions

19

(1)

Stereochemistry of Electrocyclic Reactions

20

(1)

Woodward-Hoffmann Rules for Electrocyclic Reactions

21

(11)

Frontier Orbital Method of Analysis of Electrocyclic Reactions

21

(2)

Orbital Symmetry Correlation Method for the Electrocyclic Reactions

23

(8)

Transition State Aromaticity Method

31

(1)

Electrocyclic Reactions Exemplified

32

(50)

Three-membered Ring Systems

32

(5)

Four-membered Ring Systems

37

(11)

Five-membered Ring Systems

48

(9)

Six-membered Ring Systems

57

(10)

Seven-membered Ring Systems

67

(2)

Eight-membered Ring Systems

69

(2)

Miscellaneous Higher Order Systems

71

(4)

References

75

(7)

Cycloaddition Reactions

82

(133)

Definition

82

(1)

Classification

82

(1)

Stereochemistry of Cycloaddition Reactions

83

(1)

Woodward-Hoffmann Rules for Cycloaddition Reactions

84

(6)

Frontier Orbital Method

84

(2)

Orbital Correlation Method

86

(4)

Transition State Aromaticity Method

90

(1)

Illustrations of Cycloaddition Reactions

90

(16)

[2π + 2π] Cycloadditions

90

(1)

Photochemical [2π + 2π] Cycloadditions

91

(7)

Thermal [2πs + 2πa] Cycloadditions

98

(4)

Intramolecular Cycloaddition Reactions of Ketenes

102

(4)

[4π + 2π] Cycloaddition Reactions

106

(63)

Diels-Alder Reaction

106

(1)

Diels-Alder Dienes

107

(2)

Dienophiles

109

(1)

The ``cis'' Rule

109

(2)

Alder's ``endo'' Rule

111

(3)

Regioselectivity

114

(3)

Rates of Diels-Alder Reactions

117

(2)

Diels-Alder Reaction in Organic Synthesis

119

(20)

Heterodienes and Dienophiles

139

(7)

Inverse Electron Demand Diels-Alder (IEDDA) Reactions

146

(4)

Intramolecular Diels-Alder (IDA) Reactions

150

(7)

Catalysis of Diels-Alder Reaction

157

(4)

Asymmetric Diels-Alder Reactions

161

(8)

1,3-Dipolar Cycloadditions

169

(3)

Mechanism of 1,3-Dipolar Cycloadditions

171

(1)

Synthetic Applications of 1,3-Dipolar Cycloadditions

172

(19)

Nitrones

172

(7)

Azomethine ylids

179

(6)

Nitrile oxides

185

(6)

Higher order cycloaddition reactions

191

(24)

[4π + 4π] Cycloadditions

191

(2)

[6π + 4π] Cycloadditions

193

(2)

[8π + 2π] Cycloadditions

195

(1)

[14π + 2π] Cycloadditions

196

(1)

References

197

(18)

Sigmatropic Rearrangements

215

(93)

Definition

215

(1)

Classification

215

(2)

Stereochemistry of Sigmatropic Rearrangements

217

(1)

Woodward-Hoffmann Rules for Sigmatropic Rearrangements

218

(7)

Frontier Orbital Method

218

(4)

Transition State Aromaticity Method

222

(3)

Illustrations of Sigmatropic Rearrangements

225

(83)

[1,2]-Sigmatropic Rearrangements of Carbenium Ions

225

(1)

[1,3] Sigmatropic Rearrangements

225

(8)

[1,4] Sigmatropic Rearrangements

233

(2)

[1,5] Sigmatropic Rearrangements

235

(6)

[3.3] Sigmatropic Rearrangements

241

(4)

Degenerate Cope Systems

245

(12)

Claisen Rearrangement

257

(2)

Mechanism of Claisen Rearrangement

259

(9)

Aromatic Claisen Rearrangement

268

(3)

Asymmetric [3,3] Sigmatropic Rearrangements

271

(8)

[2,3] Sigmatropic Rearrangements

279

(13)

Higher Order Sigmatropic Rearrangements

292

(5)

References

297

(11)

Chelotropic, Group Transfer and ENE Reactions

308

(53)

Chelotropic Reactions

308

(1)

Definition Chelotropic Reactions

308

(1)

Analysis of the Chelotropic Reactions

309

(1)

Woodward-Hoffmann Rules for Chelotropic Reactions

309

(3)

Chelotropic Reactions Exemplified

312

(14)

Reactions Involving SO2

312

(7)

Synthetic Applications

319

(2)

Chelotropic Extrusion of Nitrogen

321

(1)

Chelotropic Decarbonylation of Ketones

322

(3)

Chelotropic Trapping of Nitric Oxide

325

(1)

Miscellaneous Systems

326

(1)

Group Transfer Reactions

326

(1)

Definition of Group Transfer Reactions

326

(3)

Group Transfer Reactions Exemplified

328

(1)

Ene Reactions

329

(1)

Definition of Ene Reactions

329

(32)

Classification

330

(1)

Uncatalyzed all-carbon Ene Reactions

331

(2)

Uncatalyzed Intramolecular all-carbon Ene Reactions

333

(3)

Lewis acid Catalyzed Ene Reactions

336

(1)

Oxy-ene and Anionic Oxy-ene Reactions

337

(1)

Carbonyl ene reactions

338

(2)

Lewis Acid Catalyzed Carbonyl Ene Reactions

340

(3)

Imino-ene Reactions

343

(3)

Singlet Oxygen Ene Reactions

346

(1)

Stereochemistry of Ene Reactions -- Diastereoselection

346

(3)

Asymmetric Ene Reactions

349

(4)

Retro Ene Reactions

353

(1)

References

354

(7)

Special Topics

361

(50)

Organometallic Pericyclic Reactions

361

(13)

Introduction

361

(1)

Electrocyclic Reactions

361

(4)

Sigmatropic Rearrangements

365

(5)

Cycloaddition Reactions

370

(3)

Organometallic Ene Reactions

373

(1)

Pericyclic Reactions of Radical Cations

374

(19)

Introduction

374

(1)

Generation of Radical Cations

375

(2)

Electrocyclic Reactions

377

(3)

Radical Cation Cycloadditions

380

(1)

Radical Cation Cyclobutanation Reactions

381

(4)

Radical Cation Diels-Alder Reactions

385

(8)

Periselectivity

393

(6)

Definition

393

(1)

Examples of Periselectivity

393

(6)

Symmetry Forbidden Concerted Processes: Violation of Woodward-Hoffmann Rules?

399

(12)

Introduction

399

(1)

Examples of Symmetry Forbidden Reactions

400

(5)

References

405

(6)

Subject Index

411

(6)

Author Index

417

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Pericyclic Reactions - A Textbook Reactions, Applications and Theory

Summary

Author Biography

Table of Contents

Supplemental Materials