Polycyclic Aromatic Hydrocarbons

Polycyclic aromatic hydrocarbons (PAHs) have found applications in a variety of industries including dyes, drugs, semiconductors, fluorescent reagents, chemiluminescent reagents, and as polychromatic and antistatic additives for plastics. This up-to-date, single volume reference source brings together all essential information on the physical and spectral properties, methods of synthesis, and chemical reactivity of PAHs, both alternant and nonalternant. The title also covers the investigations of PAHs as carcinogens and pollutants. As this important class of molecules are virtually ignored in most chemistry programs, this book will be a strong addition to the work of anyone involved in any aspect of polycyclic aromatic hydrocarbons, chemical carcinogenesis, and environmental pollution.

Ronald G. Harvey is the author of Polycyclic Aromatic Hydrocarbons, published by Wiley.

Preface

xi

Chapter 1 Introduction

1

(20)

1.1 Importance

1

(7)

1.2 Environmental Occurrence and Biological Importance

8

(4)

1.3 Nomenclature

12

(5)

1.4 Classification of Polyarenes

17

(2)

1.5 References

19

(2)

Chapter 2 Structure and Aromaticity

21

(22)

2.1 Historical

21

(1)

2.2 Aromaticity

22

(4)

2.3 Bond Order and Bond Length

26

(1)

2.4 Molecular Structure and Bond Localization

27

(8)

2.5 Planarity and X-Ray Analysis

35

(4)

2.6 Diamagnetic Susceptibility

39

(1)

2.7 References

40

(3)

Chapter 3 General Synthetic Methods

43

(46)

3.1 Cyclodehydration Methods

43

(16)

3.2 Diels-Alder Cycloaddition

59

(3)

3.3 Photocyclization

62

(4)

3.4 Flash Vacuum Pyrolysis (Thermolysis)

66

(2)

3.5 Cyclodehydrogenation

68

(3)

3.6 Wittig-Type Reactions

71

(1)

3.7 Rearrangements and Ring Expansion

72

(1)

3.8 Cyclization of bis-Halomethyl Compounds

72

(1)

3.9 Jutz Synthesis

73

(1)

3.10 Cyclodehydrohalogenation

74

(1)

3.11 Diaryl Coupling

75

(1)

3.12 Elbs Reaction

76

(1)

3.13 Pschorr Synthesis

76

(2)

3.14 Reductive Cyclization of Dialdehydes with Hydrazine

78

(1)

3.15 Cyclization with Extrusion of Sulfur or Nitrogen

78

(2)

3.16 Annelation of Quinones

80

(1)

3.17 Dehydrogenation of Hydroaromatic Compounds

80

(1)

3.18 Dimerization and Trimerization of Acetylenes and Arynes

81

(2)

3.19 Reduction of Quinones, Hydroquinones, and Phenols

83

(1)

3.20 References

84

(5)

Chapter 4 Reactions

89

(40)

4.1 Electrophilic Substitutions

90

(9)

4.2 Nucleophilic and Free Radical Reactions

99

(1)

4.3 Addition Reactions

100

(5)

4.4 Reduction and Reductive Alkylation

105

(5)

4.5 Oxidation

110

(8)

4.6 Rearrangements of Aromatic Ring Systems

118

(3)

4.7 Complex Formation

121

(2)

4.8 References

123

(6)

Chapter 5 Alternant Polyarenes with Five Rings

129

(60)

5.1 Pentacene

130

(6)

5.2 Benzo[a]naphthacene

136

(2)

5.3 Pentaphene

138

(2)

5.4 Dibenz[a,c]anthracene

140

(4)

5.5 Dibenz[a,h]anthracene

144

(4)

5.6 Dibenz[a,j]anthracene

148

(2)

5.7 Naphth[1,2-a]anthracene

150

(1)

5.8 Perylene

151

(5)

5.9 Benzo[a]pyrene

156

(7)

5.10 Benzo[e]pyrene

163

(6)

5.11 Benzo[b]chrysene

169

(1)

5.12 Benzo[c]chrysene

169

(2)

5.13 Benzo[g]chrysene

171

(3)

5.14 Picene

174

(2)

5.15 Dibenzo[c,g]phenanthrene

176

(2)

5.16 References

178

(11)

Chapter 6 Alternant Polyarenes with Six Rings

189

(58)

6.1 Cata-Condensed

189

(31)

6.2 Peri-Condensed

220

(20)

6.3 References

240

(7)

Chapter 7 Alternant Polyarenes with Seven Rings

247

(80)

7.1 Cata-Condensed with Four to Seven Linear Fused Rings

248

(16)

7.2 Cata-Condensed with Three Linear Fused Rings

264

(14)

7.3 Cata-Condensed with Two Linear Fused Rings

278

(7)

7.4 Peri-Condensed with Five Linear Fused Rings

285

(4)

7.5 Peri-Condensed with Four Linear Fused Rings

289

(17)

7.6 Peri-Condensed with Three Linear Fused Rings

306

(15)

7.7 References

321

(6)

Chapter 8 Nonalternant Polyarenes with Four Fused Rings

327

(52)

8.1 Fluoranthene

329

(7)

8.2 4H-Cyclopenta[def]phenanthrene

336

(5)

8.3 Aceanthrylene

341

(2)

8.4 Acephenanthrylene

343

(1)

8.5 11H-Benzo[a]fluorene

344

(2)

8.6 11H-Benzo[b]fluorene

346

(1)

8.7 7H-Benzo[c]fluorene

346

(2)

8.8 Cyclopent[f,g]acenaphthylene

348

(2)

8.9 Indeno[2,1-a]indene

350

(3)

8.10 Indeno[1,2-a]indene

353

(1)

8.11 Cyclopenta[def]fluorene

354

(2)

8.12 Benz[e]-as-indacene

356

(1)

8.13 2H- and 9bH-Cyclopenta[jk]fluorene

356

(2)

8.14 7H-Benz[de]anthracene

358

(9)

8.15 1H-Benz[de]anthracene

367

(1)

8.16 3H-Benz[de]anthracene

368

(1)

8.17 Benzo[a]biphenylene

368

(2)

8.18 Benzo[b]biphenylene

370

(1)

8.19 References

371

(8)

Chapter 9 Nonalternant Polyarenes with Five Fused Rings

379

(100)

9.1 Phenalenes

379

(18)

9.2 Fluoranthenes and Acenaphthenes

397

(31)

9.3 Fluorenes

428

(28)

9.4 Biphenylenes

456

(13)

9.5 References

469

(10)

Chapter 10 Nonalternant Polyarenes with Six Fused Rings

479

(90)

10.1 Phenalenes

480

(18)

10.2 Fluoranthenes

498

(18)

10.3 Fluorenes

516

(14)

10.4 Methylene-Bridged Polyarenes

530

(14)

10.5 Acenaphthylenes

544

(3)

10.6 Biphenylenes

547

(7)

10.7 Hybrid Ring Systems

554

(9)

10.8 References

563

(6)

Chapter 11 Nonalternant Polyarenes with Seven Fused Rings

569

(73)

11.1 Phenalenes

570

(10)

11.2 Fluoranthenes

580

(16)

11.3 Fluorenes

596

(20)

11.4 Acenaphthylenes

616

(2)

11.5 Biphenylenes

618

(9)

11.6 Hybrid Ring Systems

627

(11)

11.7 References

638

(4)

Index

642

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Polycyclic Aromatic Hydrocarbons

Summary

Author Biography

Table of Contents

Supplemental Materials