Classics in Hydrocarbon Chemistry. By Henning Hopf

Carbon and Hydrogen: the two basic building units can be combined in a million different ways to give a plethora of fascinating organic compounds. Henning Hopf presents not only the most remark- able structures and properties of hydrocarbon compounds but shows in a clear presentation and with great didactic skill how molecules like tetrahedrane, superphane or dodecahedrane challenge the syn- thetic skills of every organic chemist. To make the information more accessible, especially to the nov- ice, the author carefully analyzes the synthetic problem and 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 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.

Below is the Table of Contents:

1 -Preface -1. 2 -From Simple Building Blocks to -Complex Target Molecules and Multifaceted Re- actions -5. 3 -Adamantane and other Cage Hydrocarbons -23. 3.1 -Adamantane -23. 3.2 -Higher ana-logs of adamantane -29. 3.3 -Twistane -30. 3.4 -Tetraasterane -34. -References -37. 4 -The Prismanes -41. 4.1 -Triprismane -42. 4.2 -[5]-Prismane -44. 4.3 -En route to hexaprismane -47 -References -50. 5 -The Platonic Hydrocarbons -53. 5.1 -Tetrahedrane -54. 5.2 -Cubane ([4]-prismane) -60. 5.3 -Dodecahedrane -63 -References -75. 6 -Bridgehead-distorted Hydrocarbons -81. 6.1 -Propellanes -82. 6.2 -Fenestranes -88. 6.3 -out,out, out,in and in,in Hydrocarbons -94 -References -99. 7 -Alkenes -1037.1 -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 prepa- rative futility -138 -References -142. 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 -References -165. 9 - Allenes and Cumulenes -171. 9.1 -Acyclic allenes -171. 9.2 -Acyclic cumulenes -178. 9.3 -Cyclic al- lenes -182. 9.4 -Cyclic cumulenes -188 -References -190. 10 -The Annulenes -197. 10.1 -1,3- Cyclobutadiene -198. 10.2 -Benzene and its isomers -203. 10.3 -Cyclooctatetraene and the (CH)8 iso- mers -209. 10.4 -The higher annulenes -218. 10.5 -Bridged annulenes -227 -References -238. 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 -References -309. 12 -Leaving the p- Plane-Non-Planar Aromatic Compounds -32112.1 -The helicenes -323. 12.2 -The circulenes -330. 12.3 -The cyclophanes -337 -References -368. 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 -References -412. 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 -References -443. 15 -Extended Systems-II. Beyond the PAH Pattern -447. 15.1 -From biphenyl- ene to linear and angular [n]phenylenes -447. 15.2 -Extended structures containing triple bonds -457. 15.3 -Building with cyclopropane rings -472 -References -480. 16 -Classics in Hydrocarbon Synthesis- -Three Examples from Physical Organic Chemistry -48516.1 -The dehydrobenzenes -485. 16.2 -Non- Kekulé hydrocarbons -492. 16.3 -Bond fixation in benzene rings -501 -References -514 -Author Index -523 -Subject Index -527.

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