Classics in Hydrocarbon Chemistry
Syntheses, Concepts, Perspectives
1. Edition March 2000
XIII, 547 Pages, Softcover
434 Pictures
Textbook
Short Description
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 remarkable 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 synthetic skills of every organic chemist. Graduate students and researchers alike will find this book a gold mine of useful information essential for their daily work.
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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 remarkable 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 synthetic skills of every organic chemist. To make the information more accessible, especially to the novice, 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
FROM SIMPLE BUILDING BLOCKS TO COMPLEX TARGET MOLECULES AND MULTIFACETED REACTIONS
ADAMANTANE AND OTHER CAGE HYDROCARBONS
Adamantane
Higher analogs of adamantane
Twistane
Tetraasterane
References
THE PRISMANES
Triprismane
[5]-Prismane
En route to hexaprismane
References
THE PLATONIC HYDROCARBONS
Tetrahedrane
Cubane ([4]-prismane)
Dodecahedrane
References
BRIDGEHEAD-DISTORTED HYDROCARBONS
Propellanes
Fenestranes
out,out, out,in and in,in Hydrocarbons
References
ALKENES
Linear conjugated polyenes
Cyclopropene, the smallest cycloolefin and how it can be used in hydrocarbon synthesis
Large-ring cycloalkenes by transition metal-catalyzed oligomerization of dienes
Distorted olefins: trans-cycloalkenes, anti-Bredt-hydrocarbons, betweenanenes, and pyramidalized olefins
Tetrakis-tert-butylethene - an exercise in preparative futility
References
ALKYNES
Polyacetylenes - rods made of carbon
Angle-strained cycloalkynes
Medium and large-ring alkynes
References
ALLENES AND CUMULENES
Acyclic allenes
Acyclic cumulenes
Cyclic allenes
Cyclic cumulenes
References
THE ANNULENES
1,3-Cyclobutadiene
Benzene and its isomers
Cyclooctatetraene and the (CH)8 isomers
The higher annulenes
Bridged annulenes
References
CROSS-CONJUGATED AND RELATED HYDROCARBONS
The dendralenes
The fulvenes
The fulvalenes
Pentalene, azulene, heptalene and other zero-bridged annulenes
The [n]radialenes
The [n]rotanes
References
LEAVING THE P-PLANE-NON-PLANAR AROMATIC COMPOUNDS
The helicenes
The circulenes
The cyclophanes
References
THREE-DIMENSIONAL OLIGOOLEFINS
Barrelene
Triptycene and the iptycenes
Bullvalene and semibullvalene
Triquinacene
Spiropolyenes, stellapolyenes and related hydrocarbons
References
EXTENDED SYSTEMS I. FROM BENZENE TO GRAPHITE SUBSTRUCTURES
Linearly annelated polycyclic aromatic hydrocarbons
Angularly annelated polycyclic aromatic hydrocarbons
Condensed aromatic hydrocarbons with ribbon structures
Graphite substructures
References
EXTENDED SYSTEMS II. BEYOND THE PAH PATTERN
From biphenylene to linear and angular [n]phenylenes
Extended structures containing triple bonds
Building with cyclopropane rings
References
CLASSICS IN HYDROCARBON SYNTHESIS: THREE EXAMPLES FROM PHYSICAL ORGANIC CHEMISTRY
The dehydrobenzenes
Non-Kekulé hydrocarbons
Bond fixation in benzene rings
References
Author Index
Subject Index
"I recommend this book to anyone interested in the synthesis of' organic compounds. The price tag puts this book well within the reach of personal collections, and I would expect all good chemistry libraries to have a copy on the shelves." Chemistry in Britain
"...an essential reference work to all teachers of organic chemistry and as a source of inspiration to the organic chemistry community in general." Chemistry & Industry
"...a mandatory purchase for all chemistry libraries and is a book that will rightly find its place in the personal collections of organic chemists of all denominations... a terrific resource for both research and teaching and I wholeheartedly recommend it." Journal of the Chemical Society
"This monograph is a terrific resource for both research and teaching and I wholeheartedly recommend it."
PERKINTRANSACTIONS, 2001; Vol. 9
