Halogenated pyridines can be used as interesting starting materials in a wide range of organic synthesis methods. Substituted pyridine compounds are used generally as starting materials in the nucleophilic substitution reactions and have unique scaffolds for the construction of other heterocyclic and macrocyclic compounds. They also have important medicinal properties. Due to synthetic difficulties in the synthesis of the highly substituted pyridine derivatives from pyridine itself, perhalopyridines have a special importance in this regard. This book covers the synthetic reactions and applications of perhalopyridines.
An introductory chapter introduces the reader to the physical and chemical properties of halopyridines, followed by 3 chapters which focus on pentafluoropyridine, pentachloropyridine and pentabromopyridine, respectively. The focused chapters provide information about synthetic methods and relevant nucleophilic reactions for each of the listed perhalopyridines and their derivatives. The book is a quick reference on perhalopyridines for students of applied chemistry, organic chemistry and chemical engineering.
Table of Contents
CHAPTER 1 PROPERTIES OF PERHALOPYRIDINES
1. Physical and Chemical Properties
2. Spectroscopy
3. Reactions References
CHAPTER 2 PERFLUOROPYRIDINES
1. Introduction
2. Synthesis of Pentafluoropyridine
3. Reaction Mechanism
4. Reaction of Pentafluoropyridine with Various Mono Dentate Nucleophiles
4.1. Reaction of S-Centered Nucleophile with Pentafluoropyridine
4.2. Reaction of O-Centered Nucleophile with Pentafluoropyridine
4.3. Reaction of C-Centered Nucleophile with Pentafluoropyridine
4.4. Reaction of N-Centered Nucleophile with Pentafluoropyridine
4.5. Reaction of Pentafluoropyridine 3 with Halogenating Reagents (Cl, Br, I)
4.6. Reduction of Perfluorinated Pyridines
5. Reaction of Perfluoropyridines with Various Multidentate Nucleophiles
5.1. Synthesis of Perfluorinated Heterocyles
5.2. Synthesis of Fluorinated Ring-Fused Heterocyles
6. Organometallic Compounds of Perfluoro- Heteroaromatics
7. Photochemical Reactions of Fluorinated Pyridines
8. Copolymerization of Pentafluoropyridine
9. the Pentafluoropyridine Cation C5F5N+
10. Salts of Perfluoropyridine
11. Synthesis of Macrocyclic Compounds from Polyfluoropyridines
12. Pentafluoropyridine in Medicinal Chemistry and Biochemistry References
CHAPTER 3 PERCHLOROPYRIDINES
1. Introduction
2. Synthesis of Pentachloropyridine
2.1. by Straight Chlorination
2.2. by Ring-Closing Method
2.3. Synthesis of Pentachloropyridine-1-15N-2,6-13C2
3. Nucleophilic Reactions of Perchloropyridines
3.1. Reaction of Pentachloropyridine with Various Mono Dentate Nucleophiles
3.1.1. Reaction of N-Centered Nucleophile with Pentachloropyridine
3.1.2. Reaction of S-Centered Nucleophile with Pentachloropyridine
3.1.3. Reaction of C-Centered Nucleophile with Perchloropyridines
3.2. Reaction of Perchloropyridines with Bidentate Nucleophiles
4. Cross-Coupling Reactions of Perchloropyridines
5. Bromination of Pentachloropyridine
6. Oxidation of Polychloropyridines
7. Reduction of Polychloropyridines
8. Alkylation of Polychloropyridines
9. Photochemical Reactions of Polychloropyridines
10. Organometallic Reagents of Perchloropyridine References
CHAPTER 4 PERBROMOPYRIDINES
1. Synthesis of Pentabromopyridine
2. Nucleophilic Reactions of Pentabromopyridine
2.1. Reaction of O-Centered Nucleophile with Pentabromopyridine
2.2. Reaction of N-Centered Nucleophile with Pentabromopyridine
2.3. Reaction of S-Centered Nucleophile with Pentabromopyridine
3. Organometalic Reagent of Polybromopyridines
4. Salts of Pentabromopyridine
5. Oxidation of Pentabromopyridine
6. Photochemical Reactions of Pentabromopyridine
7. Synthesis and Reactions of 2,4,6-Tribromo-3,5-Difluoropyridine
8. Synthesis and Reactions of 3,5-Dibromo-2,6-Dichloropyridine
References
Subject Index
Samples
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Author
- Alireza Poorfreidoni
- Reza Ranjbar-Karimi
