The Porphyrins V2

The Porphyrins, Volume II: Structure and Synthesis, Part B is devoted to the structure and synthesis of porphyrins, their precursors, catabolic derivatives, and related systems. The book also covers nomenclature, history, geochemistry, purification, and structural determination of porphyrins, metalloporphyrins, and mono- and polypyrrolic compounds. This volume is organized into 10 chapters and begins with an overview of hydroporphyrins, paying particular attention to their synthesis and stereochemistry as well as reactivity, spectroscopy, and analogues. This book then discusses the synthesis, properties, thermodynamic stability, and evolution of porphyrinogens. The following chapters focus on porphyrins reversibly modified at the periphery by oxidation (oxophlorins) and by irreversible reactions at the periphery. The synthesis of photoexcited porphyrins, metalloporphyrins, and chlorophylls is covered. In addition, chapters on linear polypyrroles, their metal complexes, and macrocycles other than porphyrins are included. This book should be useful to inorganic, organic, physical, and biochemists interested in porphyrin chemistry and biochemistry.

List of Contributors

General Preface

Preface

Contents of Other Volumes

1 Synthesis and Stereochemistry of Hydroporphyrins

I. Introduction

II. Synthesis of Hydroporphyrins

III. Stereochemistry

IV. Conclusions

V. Appendix: Recent Studies in Chlorophyll Chemistry

References

2 Hydroporphyrins: Reactivity, Spectroscopy, and Hydroporphyrin Analogues

I. Reactivity of Hydroporphyrins

II. Spectroscopy of Hydroporphyrins

III. Oxy and Oxo Analogues of the Hydroporphyrins

References

3 The Porphyrinogens

I. Introduction

II. Synthesis

III. Properties

IV. Thermodynamic Stability and Evolution

References

4 Oxophlorins (Oxyporphyrins)

I. Introduction

II. Preparation of the Oxophlorins

III. Properties of the Oxophlorins

IV. Oxidation of Hemes

References

5 Irreversible Reactions on the Porphyrin Periphery (Excluding Oxidations, Reductions, and Photochemical Reactions)

I. Reactivity Patterns of the Porphyrin Periphery

II. Introduction of Carbon Substituents into the Porphyrin Periphery

III. Introduction of Nitrogen Substituents into the Porphyrin Periphery

IV. Introduction of Sulfur Substituents into the Porphyrin Periphery

V. Halogenation of the Porphyrin Periphery

References

6 Chemical Transformations Involving Photoexcited Porphyrins and Metalloporphyrins

I. Introduction

II. Photoprocesses Not Involving Permanent Transformation of the Porphyrin

III. Photoprocesses Involving Permanent Transformations of the Porphyrin

References

7 Linear Polypyrrolic Compounds

I. Introduction

II. Nomenclature

III. Bipyrrolic Compounds

IV. Tripyrrolic Compounds

V. Tetrapyrrolic Compounds

References

8 Metal Complexes of Open-Chain Tetrapyrrole Pigments

I. Introduction

II. Composition and Electronic and Vibrational Spectra of Open-Chain Tetrapyrrolic Metal Complexes

III. EPR Studies

IV. X-Ray Structures

V. Chemical Reactivity

VI. A Comparison of Open-Chain Tetrapyrrole Chromophores with Related Macrocyclic Systems

References

9 Stereochemistry and Absolute Configuration of Chlorophylls and Linear Tetrapyrroles

I. Introduction

II. Chlorophylls of Higher Plants

III. Bacterial Chlorophylls

IV. Stereochemistry of the Esterifying Alcohols

V. Linear Tetrapyrroles

References

10 Pyrrolic Macrocycles Other than Porphyrins

I. Corroies

II. 22π-Electron Macrocycles: Sapphyrins and Related Compounds

III. 1-Substituted and 1,19-Disubstituted Metallotetradehydrocorrins

IV. 1-Substituted and 1,19-Disubstituted Corrins

References

Author Index

Subject Index