Organic Mechanisms: Reactions, Stereochemistry and Synthesis

Front Cover
Springer Science & Business Media, Jan 20, 2010 - Science - 855 pages
This English edition of a best-selling and award-winning German textbook Reaction Mechanisms: Organic Reactions · Stereochemistry · Modern Synthetic Methods is aimed at those who desire to learn organic chemistry through an approach that is facile to understand and easily committed to memory. Michael Harmata, Norman Rabjohn Distinguished Professor of Organic Chemistry (University of Missouri) surveyed the accuracy of the translation, made certain contributions, and above all adapted its rationalizations to those prevalent in the organic chemistry community in the English-speaking world. Throughout the book fundamental and advanced reaction mechanisms are presented with meticulous precision. The systematic use of red "electron-pushing arrows" allows students to follow each transformation elementary step by elementary step. Mechanisms are not only presented in the traditional contexts of rate laws and substituent effects but, whenever possible, are illustrated using practical, useful and state-of-the-art reactions. The abundance of stereoselective reactions included in the treatise makes the reader familiar with key concepts of stereochemistry. The fundamental topics of the book address the needs of upper-level undergraduate students, while its advanced sections are intended for graduate-level audiences. Accordingly, this book is an essential learning tool for students and a unique addition to the reference desk of practicing organic chemists, who as life-long learners desire to keep abreast of both fundamental and applied aspects of our science. In addition, it will well serve ambitious students in chemistry-related fields such as biochemistry, medicinal chemistry and pharmaceutical chemistry. From the reviews: "Professor Bruckner has further refined his already masterful synthetic organic chemistry classic; the additions are seamless and the text retains the magnificent clarity, rigour and precision which were the hallmark of previous editions. The strength of the book stems from Professor Bruckner’s ability to provide lucid explanations based on a deep understanding of physical organic chemistry and to limit discussion to very carefully selected reaction classes illuminated by exquisitely pertinent examples, often from the recent literature. The panoply of organic synthesis is analysed and dissected according to fundamental structural, orbital, kinetic and thermodynamic principles with an effortless coherence that yields great insight and never over-simplifies. The perfect source text for advanced Undergraduate and Masters/PhD students who want to understand, in depth, the art of synthesis ." Alan C. Spivey, Imperial College London "Bruckner’s ‘Organic Mechanisms’ accurately reflects the way practicing organic chemists think and speak about organic reactions. The figures are beautifully drawn and show the way organic chemists graphically depict reactions. It uses a combination of basic valence bond pictures with more sophisticated molecular orbital treatments. It handles mechanisms both from the "electron pushing perspective" and from a kinetic and energetic view. The book will be very useful to new US graduate students and will help bring them to the level of sophistication needed to be serious researchers in organic chemistry." Charles P. Casey, University of Wisconsin-Madison "This is an excellent advanced organic chemistry textbook that provides a key resource for students and teachers alike." Mark Rizzacasa, University of Melbourne, Australia.
 

Contents

Radical Substitution Reactions at the Saturated C Atom
1
Nucleophilic Substitution Reactions at the Saturated C Atom
53
on Reactivity
60
Electrophilic Additions to the CC Double Bond 103
102
as cisAdditions
109
bEliminations
157
Substitution Reactions on Aromatic Compounds
201
Aryllithium Compounds That Are Accessible from Aryl Halides
237
Addition of Hydride Donors and of Organometallic Compounds
397
Conversion of Phosphorus or SulfurStabilized C Nucleophiles
456
The Chemistry of Enols and Enamines
487
Tautomeric Enols
493
Chemistry of the Alkaline Earth Metal Enolates 519
518
Synthesis of bHydroxyketones and bHydroxyesters
558
Michael Acceptors
565
Rearrangements
595

Nucleophilic Substitution Reactions at the Carboxyl Carbon 259
258
Carboxylic Compounds Nitriles and Their Interconversion
321
Acid Derivatives
328
Carbonic Acid Derivatives and Heterocumulenes
339
Additions of Heteroatom Nucleophiles to Carbonyl Compounds
359
Thermal Cycloadditions
643
Transition MetalMediated Alkenylations Arylations
690
Oxidations and Reductions
737
Subject Index
827
Copyright

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