Classics in hydrocarbon chemistry : syntheses, concepts, perspectives / Henning Hopf.

Format:

Book

Author/Creator:

Hopf, Henning, 1940-

Language:

English

Subjects (All):

Hydrocarbons--Synthesis.

Hydrocarbons.

Organic compounds--Synthesis.

Organic compounds.

Physical Description:

xiii, 547 pages : illustrations ; 24 cm

Place of Publication:

Weinheim ; New York : Wiley-VCH, [2000]

Summary:

Brings together many of the most important advances in organic chemistry of the last century and can be read at several levels.

Contents:

2 From Simple Building Blocks to Complex Target Molecules and Multifaceted Reactions 5

3 Adamantane and other Cage Hydrocarbons 23

3.1 Adamantane 23

3.2 Higher analogs of adamantane 29

3.3 Twistane 30

3.4 Tetraasterane 34

4 The Prismanes 41

4.1 Triprismane 42

4.2 [5]-Prismane 44

4.3 En route to hexaprismane 47

5 The Platonic Hydrocarbons 53

5.1 Tetrahedrane 54

5.2 Cubane ([4]-prismane) 60

5.3 Dodecahedrane 63

6 Bridgehead-distorted Hydrocarbons 81

6.1 Propellanes 82

6.2 Fenestranes 88

6.3 Out, out, out, in and in, in Hydrocarbons 94

7 Alkenes 103

7.1 Linear conjugated polyenes 103

7.2 Cyclopropene, the smallest cycloolefin and how it can be used in hydrocarbon synthesis 112

7.3 Large-ring cycloalkenes by transition metal-catalyzed oligomerization of dienes 118

7.4 Distorted olefins: trans-cycloalkenes, anti-Bredt-hydrocarbons, betweenanenes, and pyramidalized olefins 122

7.5 Tetrakis-tert-butylethene - an exercise in preparative futility 138

8 Alkynes 151

8.1 Polyacetylenes - rods made of carbon 151

8.2 Angle-strained cycloalkynes 156

8.3 Medium and large-ring alkynes 160

9 Allenes and Cumulenes 171

9.1 Acyclic allenes 171

9.2 Acyclic cumulenes 178

9.3 Cyclic allenes 182

9.4 Cyclic cumulenes 188

10 The Annulenes 197

10.1 1,3-Cyclobutadiene 198

10.2 Benzene and its isomers 203

10.3 Cyclooctatetraene and the (CH)[subscript 8] isomers 209

10.4 The higher annulenes 218

10.5 Bridged annulenes 227

11 Cross-Conjugated and Related Hydrocarbons 251

11.1 The dendralenes 253

11.2 The fulvenes 260

11.3 The fulvalenes 269

11.4 Pentalene, azulene, heptalene and other zero-bridged annulenes 277

11.5 The [n]radialenes 290

11.6 The [n]rotanes 300

12 Leaving the [pi]-Plane

Non-Planar Aromatic Compounds 321

12.1 The helicenes 323

12.2 The circulenes 330

12.3 The cyclophanes 337

13 Three-dimensional Oligoolefins 379

13.1 Barrelene 380

13.2 Triptycene and the iptycenes 385

13.3 Bullvalene and semibullvalene 389

13.4 Triquinacene 397

13.5 Spiropolyenes, stellapolyenes and related hydrocarbons 407

14 Extended Systems-I. From Benzene to Graphite Substructures 421

14.1 Linearly annelated polycyclic aromatic hydrocarbons 423

14.2 Angularly annelated polycyclic aromatic hydrocarbons 426

14.3 Condensed aromatic hydrocarbons with ribbon structures 431

14.4 Graphite substructures 438

15 Extended Systems-II. Beyond the PAH Pattern 447

15.1 From biphenylene to linear and angular [n]phenylenes 447

15.2 Extended structures containing triple bonds 457

15.3 Building with cyclopropane rings 472

16 Classics in Hydrocarbon Synthesis

Three Examples from Physical Organic Chemistry 485

16.1 The dehydrobenzenes 485

16.2 Non-Kekule hydrocarbons 492

16.3 Bond fixation in benzene rings 501.

Notes:

Includes bibliographical references and index.

"With a foreword by W. von Eggers Doering."

ISBN:

3527296069

OCLC:

41961065