Side Reactions in Organic Synthesis. A Guide to Successful Synthesis Design

  • ID: 2179580
  • Book
  • 389 Pages
  • John Wiley and Sons Ltd
1 of 4
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 advanced 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 student but also for every chemist in industry and academia.

From The Contents:

Organic Synthesis: General Remarks

Stereoelectronic Effects and Reactivity

The Stability of Organic Compounds

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

The Alkylation of Carbanions

The Alkylation of Heteroatoms

The Acylation of Heteroatoms

Palladium–Catalyzed C–C Bond Formation

Cyclizations

Monofunctionalization of Symmetric Difunctional Substrates

Note: Product cover images may vary from those shown
2 of 4
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

Note: Product cover images may vary from those shown
3 of 4

Loading
LOADING...

4 of 4
Florencio Zaragoza Dörwald
Note: Product cover images may vary from those shown
5 of 4
Note: Product cover images may vary from those shown
Adroll
adroll