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Side Reactions in Organic Synthesis. A Guide to Successful Synthesis Design. Edition No. 1

  • ID: 2179580
  • Book
  • November 2004
  • 389 Pages
  • John Wiley and Sons Ltd
Most syntheses in the chemical research laboratory fail and usually require several attempts before proceeding satisfactorily. Failed syntheses are not only discouraging and frustrating, but also cost a lot of time and money. Many failures may, however, be avoided by understanding the structure-reactivity relationship of organic compounds.
This textbook highlights the competing processes and limitations of the most important reactions used in organic synthesis. By allowing chemists to quickly recognize potential problems this book will help to improve their efficiency and success-rate. A must for every graduate student but also for every chemist in industry and academia.

Contents:

1 Organic Synthesis: General Remarks
2 Stereoelectronic Effects and Reactivity
3 The Stability of Organic Compounds
4 Aliphatic Nucleophilic Substitutions: Problematic Electrophiles
5 The Alkylation of Carbanions
6 The Alkylation of Heteroatoms
7 The Acylation of Heteroatoms
8 Palladium-Catalyzed C-C Bond Formation
9 Cyclizations
10 Monofunctionalization of Symmetric Difunctional Substrates
Note: Product cover images may vary from those shown
ORGANIC SYNTHESIS: GENERAL REMARKS
Introduction
Synthesis Design
Hard and Soft Acids and Bases
The Curtin-Hammett Principle
STEREOELECTRONIC EFFECTS AND REACTIVITY
Hyperconjugation with sigma Bonds
Hyperconjugation with Lone Electron Pairs
Hyperconjugation and Reactivity
Conclusion
THE STABILITY OF ORGANIC COMPOUNDS
Introduction
Strained Bonds
Incompatible Functional Groups
Conjugation and Hyperconjugation of Incompatible Functional Groups
Stability towards Oxygen
Detonations
ALIPHATIC NUCLEOPHILIC SUBSTITUTIONS: PROBLEMATIC ELECTROPHILES
Mechanisms of Nucleophilic Substitution
Structure of the Leaving Group
Structure of the Electrophile
THE ALKYLATION OF CARBANIONS
Introduction
The Kinetics of Deprotonations
Regioselectivity of Deprotonations and Alkylations
The Stability of Carbanions
THE ALKYLATION OF HETEROATOMS
Alkylation of Fluoride
Alkylation of Aliphatic Amines
Alkylation of Anilines
Alkylation of Alcohols
Alkylation of Phenols
Alkylation of Amides
Alkylation of Carbamates and Ureas
Alkylation of Amidines and Guanidines
Alkylation of Carboxylates
THE ACYLATION OF HETEROATOMS
Problematic Carboxylic Acids
Problematic Amines
Problematic Alcohols
PALLADIUM-CATALYZED C-C BOND FORMATION
Introduction
Chemical Properties of Organopalladium Compounds
Mechanisms of Pd-Catalyzed C--C Bond Formation
Homocoupling and Reduction of the Organyl Halide
Homocoupling and Oxidation of the Carbon Nucleophile
Transfer of Aryl Groups from the Phosphine Ligand
Ipso- vs Cine-Substitution at Vinylboron and -tin Derivatives
Allylic Arylation and Hydrogenation as Side Reactions of the Heck Reaction
Protodemetalation of the Carbon Nucleophile
Sterically Hindered Substrates
Cyclometalation
Chelate Formation
CYCLIZATION
Introduction
Baldwin's Cyclization Rules
Structural Features of the Chain
Ring Size
Heterocycles
MONOFUNCTIONALIZATION OF SYMMETRIC DIFUNCTIONAL SUBSTRATES
Introduction
Monofunctionalization of Dicarboxylic Acids
Monofunctionalization of Diols
Monofunctionalization of Diamines
Monoalkylation of C,H-Acidic Compounds
Monoderivatization of Dihalides

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Florencio Zaragoza Dörwald Novo Nordisk A/S, Novo Nordisk Park, Malov, Denmark.
Note: Product cover images may vary from those shown
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