The two basic building units carbon and hydrogen can be combined in a million different ways to give a plethora of fascinating organic compounds. Henning Hopf presents not only the most remarkable structures and properties of hydrocarbon compounds but shows in a clear presentation and with great didactic skill how molecules like dodecahedrane, superphane or annulenes challenge the synthetic skills of every organic chemist. To make the information more accessible, especially to the novice, the author carefully analyzes the synthetic problem, explains each synthetic step and gives hints on alternative methods and potential pitfalls. Numerous references to useful reviews and the original literature make this book an indispensable source of further information. Special emphasis is placed on the skillful use of graphics and schemes: Synthetic (retro)analyses, reaction sequences, and crucial steps are presented in blue boxed sections within the text. Graduate students and researchers alike will find this book a gold mine of useful information essential for their daily work. Every organic chemist will want to have a copy on his or her desk. With a foreword by W. von Eggers Doering.

Literature Prize for Henning Hopf: Henning Hopf, Professor of Organic Chemistry at the Technische Universitaet Braunschweig (Germany), was recently awarded the German Chemical Industry Society's (VCI) Literature Prize 2001 for his monograph Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives. VCI President Manfred Schneider emphasized the powerful synthetic methods as well as the clear concept and style of the book.

Preface

1

(4)

From Simple Building Blocks to Complex Target Molecules and Multifaceted Reactions

5

(18)

Adamantane and other Cage Hydrocarbons

23

(18)

Adamantane

23

(6)

Higher analogs of adamantane

29

(1)

Twistane

30

(4)

Tetraasterane

34

(3)

References

37

(4)

The Prismanes

41

(12)

Triprismane

42

(2)

[5]-Prismane

44

(3)

En route to hexaprismane

47

(6)

References

50

(3)

The Platonic Hydrocarbons

53

(28)

Tetrahedrane

54

(6)

Cubane([4]-prismane)

60

(3)

Dodecahedrane

63

(18)

References

75

(6)

Bridgehead-distorted Hydrocarbons

81

(22)

Propellanes

82

(6)

Fenestranes

88

(6)

out, out, out, in and in, in Hydrocarbons

94

(9)

References

99

(4)

Alkenes

103

(48)

Linear conjugated polyenes

103

(9)

Cyclopropene, the smallest cycloolefin and how it can be used in hydrocarbon synthesis

112

(6)

Large-ring cycloalkenes by transition metal-catalyzed oligomerization of dienes

118

(4)

Distorted olefins: trans-cycloalkenes, anti-Bredt-hydrocarbons, betweenanenes, and pyramidalized olefins

122

(16)

Tetrakis-tert-butylethene - an exercise in preparative futility

138

(13)

References

142

(9)

Alkynes

151

(20)

Polyacetylenes - rods made of carbon

151

(5)

Angle-strained cycloalkynes

156

(4)

Medium and large-ring alkynes

160

(11)

References

165

(6)

Allenes and Cumulenes

171

(26)

Acyclic allenes

171

(7)

Acyclic cumulenes

178

(4)

Cyclic allenes

182

(6)

Cyclic cumulenes

188

(9)

References

190

(7)

The Annulenes

197

(54)

1,3-Cyclobutadiene

198

(5)

Benzene and its isomers

203

(6)

Cyclooctatetraene and the (CH)8 isomers

209

(9)

The higher annulenes

218

(9)

Bridged annulenes

227

(24)

References

238

(13)

Cross-Conjugated and Related Hydrocarbons

251

(70)

The dendralenes

253

(7)

The fulvenes

260

(9)

The fulvalenes

269

(8)

Pentalene, azulene, heptalene and other zero-bridged annulenes

277

(13)

The [n]radialenes

290

(10)

The [n]rotanes

300

(21)

References

309

(12)

Leaving the π-Plane---Non-Planar Aromatic Compounds

321

(58)

The helicenes

323

(7)

The circulenes

330

(7)

The cyclophanes

337

(42)

References

368

(11)

Three-dimensional Oligoolefins

379

(42)

Barrelene

380

(5)

Triptycene and the iptycenes

385

(4)

Bullvalene and semibullvalene

389

(8)

Triquinacene

397

(10)

Spiropolyenes, stellapolyenes and related hydrocarbons

407

(14)

References

412

(9)

Extended Systems-1. From Benzene to Graphite Substructures

421

(26)

Linearly annelated polycyclic aromatic hydrocarbons

423

(3)

Angularly annelated polycyclic aromatic hydrocarbons

426

(5)

Condensed aromatic hydrocarbons with ribbon structures

431

(7)

Graphite substructures

438

(9)

References

443

(4)

Extended Systems-II. Beyond the PAH Pattern

447

(38)

From biphenylene to linear and angular [n]phenylenes

447

(10)

Extended structures containing triple bonds

457

(15)

Building with cyclopropane rings

472

(13)

References

480

(5)

Classics in Hydrocarbon Synthesis---Three Examples from Physical Organic Chemistry

485

(38)

The dehydrobenzenes

485

(7)

Non-Kekule hydrocarbons

492

(9)

Bond fixation in benzene rings

501

(22)

References

514

(9)

Author Index

523

(4)

Subject Index

527

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