Polymers as Aids in Organic Chemistry

Preface 1. Introduction I. History II. Development of Polymer Science and Technology III. Definition and Classification of Polymers IV. Preparation of Synthetic Polymers V. Properties of Polymers VI. Synthesis of Functionalized Polymers VII. Types of Functionalized Polymers VIII. General Chemical Reactions of Polymers IX. Polymers as Aids in Organic Synthesis X. Kinetics of Polymer-Analogous Reactions XI. Literature on Solid-Phase Synthesis References 2. Polymeric Support Materials I. Introduction II. Styrene-Based Polymers III. Functionalization of Styrene-Based Polymers via Chloromethylation and Other Methods IV. Miscellaneous Polymer Supports References 3• Determination of Functionalization in Polymer Supports I. Introduction II. Chemical Methods for Functional Group Analysis of Polymers III. Physical and Physicochemical Methods of Determining Functional Groups in Polymers IV. Physical and Chemical Nature of Immobilization of Reactive Sites on Polymers V. Use of Radiolabeled Reagents to Follow the Changes in Resin Functionalities VI. Reporting of Results References 4. Polypeptide Synthesis on Polymer Supports I. Introduction and History II. Basic Principles of Merrifield's Solid-Phase Peptide Synthesis III. Supports for Solid-Phase Peptide Synthesis IV. Linkage of the First Amino Acid to the Polymer V. Protecting Groups Used in Solid-Phase Peptide Synthesis VI. Coupling of Successive Amino Acids to Resin-Bound Amino Acids VII. Cleavage of the Resin-Peptide Bond VIII. Monitoring of Solid-Phase Peptide Synthesis IX. Automation in Solid-Phase Peptide Synthesis X. Racemization Problems in Solid-Phase Peptide Products XI. Purification of Solid-Phase Peptide Products XII. Problems in Solid-Phase Synthesis XIII. Solid-Phase Coupling of N-Carboxylanhydrides (NCA) XIV. Solid-Phase Synthesis Using Side-Chain Functionalities for Attachment to Polymers and Bidirectional Extension of Peptide Chains XV. Fragment Condensation Strategy in Solid-Phase Peptide Synthesis References 5. Oligonucleotide Synthesis on Polymer Supports I. Introduction II. General Principles of Solid-Phase Oligonucleotide Synthesis III. Polymer Supports IV. Functionalization of Polymer Supports V. Strategies Used for Oligonucleotide Synthesis on Polymer Supports VI. Protection of Reactive Groups VII. Cleavage of the Protecting Groups VIII. Attachment of the Polymeric Carrier to the Nucleotide or Nucleoside IX. Elongation of the Nucleotide Chain on the Polymer Support X. Cleavage of the Polymer-Nucleoside/Nucleotide Bond XI. Monitoring in Polymer-Supported Oligonucleotide Synthesis XII. Purification of Synthetic Oligonucleotides XIII. Synthesis of Oligoribonucleotides on Polymer Supports XIV. Miscellaneous Application of Polymers in Polynucleotide Synthesis XV. Advantages and Limitations References6. Oligosaccharide Synthesis on Polymer Supports I. Introduction II. Basic Principles of Polymer-Supported Oligosaccharide Synthesis III. Polymer Supports for the Synthesis of Oligosaccharides IV. Linkage of the First Sugar Molecule to the Polymer Support and Product Removal V. Protecting Groups in Oligosaccharide Synthesis Employing Polymer Supports VI. Mechanism and Steric Control in Successive Coupling of Monosaccharide Residues on a Polymer Support VII. Miscellaneous Applications of Polymers in the Carbohydrate Field VIII. Monitoring of Solid-Phase Oligosaccharide Synthesis IX. Advantages, Limitations, and Future Scope of the Use of Polymer Supports in Polysaccharide Synthesis References 7. Peptide Synthesis Using Polymeric Active Esters I. Introduction II. Principles of Peptide Synthesis Using Polymeric Active Esters III. Polymeric Active Esters Used for Peptide Synthesis IV. Synthesis of Cyclic Peptides Using Polymeric Active Esters V. Scope and Limitations of the Polymeric Active Ester Method for Peptide Synthesis References 8. Solid-Phase Sequencing of Peptides and Proteins I. Introduction II. Solid-Phase Edman Degradation Using Polymeric Reagents III. Solid-Phase Degradation Employing Polymer-Bound Peptides IV. Other Polymer Supports for Solid-Phase Sequencing V. Attachment of the Peptide to the Polymer Support VI. Automation in Solid-Phase Sequencing VII. Solid-Phase Sequencing of Peptides from the Carboxyl Terminus VIII. Scope and Limitations of Solid-Phase Sequencing Methods References 9. Polymeric Supports in General Organic Chemistry I. Introduction II. Alkylation and Acylation of Esters Using Functionalized Carriers III. Dieckmann Cyclization of Polymer-Bound Esters IV. Cyclization of Large Ring Compounds on Polymeric Supports V. Monofunctionalization of Polymer-Bound Compounds VI. Synthesis of Threaded Macrocyclic Systems (Hooplanes) VII. Photochemical Applications References10. Polymer-Supported Asymmetric Synthesis and Resolution of Racemates Using Asymmetric Polymeric Materials I. Introduction II. Asymmetric Syntheses of Polymeric Supports III. Resolution of Racemates Using Polymeric Materials References 11. Application of Polymeric Supports in Identifying Reaction Intermediates I. Introduction II. General Strategy Used for Trapping Reaction Intermediates Employing Polymeric Supports References 12. Polymer-Bound Reagents I. Introduction II. Polymeric Oxidizing Reagents III. Polymeric Oxidation-Reduction Reagents IV. Polymeric Reducing Reagents V. Polymeric Group Transfer Reagents VI. Polymeric Coupling Agents VII. Miscellaneous Reagents References 13. Polymer-Bound Catalysts (I) I. Introduction II. Ion-Exchange Resins as General Acid-Base Catalysts III. Polystyrene-Aluminum Chloride as a Lewis Acid Catalyst IV. Polymer-Based "Super Acid" Catalysts V. Polymeric Esterolytic Catalysts VI. Polymer-Supported Phase-Transfer Catalysts VII. Polymeric Triphase Catalysts VIII. Polymer-Based Photosensitizers References 14. Polymer-Bound Catalysts (II) Transition Metal Complexes Bound to Polymers I. Polymer-Supported Transition Metal Catalysts II. Principles of Homogeneous Transition Metal Complex Catalysts III. Preparation of Polymer-Bound Transition Metal Complexes IV. Structure of Polymeric Catalysts V. Types of Reactions Catalyzed by Polymer-Anchored Catalysts VI. Asymmetric Organic Synthesis via Transition Metal Catalysts Bound to Polymeric Chiral Ligands References 15. Polymers as Aids in Related Areas of Chemistry I. Introduction II. Applications in Analytical Chemistry III. Polymer-Bound Agriculturally and Pharmacologically Active Agents IV. Applications in Biochemistry References Index