The Porphyrins V1

Structure and Synthesis, Part A

1st Edition - August 28, 1978
Editor: David Dolphin
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 4 3 7 3 - 8

The Porphyrins, Volume I: Structure and Synthesis, Part Ais the first in a series of seven volumes and covers topics like nomenclature, purification, and structural determination… Read more

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The Porphyrins, Volume I: Structure and Synthesis, Part Ais the first in a series of seven volumes and covers topics like nomenclature, purification, and structural determination of porphyrins, metalloporphyrins, and other related compounds. This volume serves to be a critical review of the topics covered and presents a complete and comprehensible discussion on the chemistry and biochemistry of porphyrins. The chapters in the text tackle the history and geochemistry of porphyrins and related systems. Also covered and discussed in the chapters is the synthesis of porphyrins from mono-, di-, and tetrapyrrolic intermediates. The isolation and modification of porphyrins from natural sources are also discussed. Other related compounds are also included, such as metallo-, aza-, and N-methylporphyrins, and their synthesis and properties. This book is a good introduction and reference for students studying in the fields of chemistry and biochemistry.

List of Contributors

General Preface

Preface

Contents of Other Volumes

1 Nomenclature

I. Introduction

II. Pyrroles

III. Systems with Two Pyrrole Rings

IV. Porphyrins and Related Compounds: The Fischer Nomenclature

V. Porphyrins and Related Compounds: A Revised Nomenclature

VI. Linear Tri- and Tetrapyrroles

VII. Ring-Contracted and Ring-Expanded Systems

VIII. Metal Complexes

References

2 Selected Landmarks in the History of Porphyrins and Their Biologically Functional Derivatives

I. Challenge of Disease States

II. Thudichum'sCruentine (Hematoporphyrin)

III. Experimental Disease States

IV. Important Books, Monographs, and Reviews

V. Conferences, Symposia, and Colloquia

VI. Determination of Iron Content of Hemoglobin (A Standard for Hemoglobinometry)

VII. Crystallization of Porphyrins, Hemes, and Hemoproteins

VIII. Hemochromogens

IX. Continuum of Concepts

X. Ongoing Problems: Return to the Functional Environment of the Cell

XI. Concluding Remarks

XII. Addendum

References

3 Synthesis of Porphyrins from Monopyrroles

I. Synthesis of Porphin and Chlorin

II. Synthesis of ß-Substituted Porphyrins

III. Synthesis of meso-Substituted Porphyrins

IV. Mechanistic Considerations

V. Cis, Trans-Dipyrrylmethene and Polypyrrylmethene Precursors

VI. Substituent Effects

VII. Cyclic Tetrapyrrole Intermediates

VIII. Conclusion

References

4 Synthesis of Pyrroles and of Porphyrins via Single-Step Coupling of Dipyrrolic Intermediates

I. Synthesis of Pyrroles from Acyclic Precursors

II. Manipulations of MonopyrrolicPorphyrin Precursors: Transformation of ß-Substituents of 5-Methylpyrrole-2-Carboxylic Esters

III. Synthesis of Dipyrrolic Intermediates and Their Conversion to Porphyrins

IV. Appendix: Selected Examples of 2 + 2 Porphyrin Syntheses

References

5 Synthesis of Porphyrins from 1,19-Dideoxybiladienes-ac and 1,19-Dideoxybilenes-b

I. Introduction

II. Linear Tetrapyrroles

References

6 Synthesis of Porphyrins from Oxobilane Intermediates

I. Introduction

II. Dipyrroketones

III. Porphyrins from a-Oxobilanes

IV. Porphyrins from b-Oxobilanes

V. Differential Protection of Pyrrole Rings

VI. Synthesis of Porphyrins Bearing Labile Groups

VII. Conclusions

References

7 Isolation and Modification of Natural Porphyrins

I. Introduction

II. Protoporphyrin and Related Natural Porphyrin Derivatives

III. Porphyrins Derived from Degradation of Chlorophylls

IV. Interconversion of Porphyrins by Chemical Means

References

8 N-Substituted Porphyrins and Corroles

I. N-Substituted Octaalkylporphyrins

II. N-Methylated Octaethylchlorins

III. N-Alkyl-meso-Tetraphenylporphyrins

IV. N-Alkylcorroles

V. N-Acetylcorroles

VI. Conclusions

References

9 Azaporphyrins

I. Introduction

II. Monoazaporphyrins

III. Diazaporphyrins

IV. Tetraazaporphyrins (Porphyrazines)

V. Phthalocyanines

VI. Analogues of the Phthalocyanines

VII. Mono-, Di-, and Triazabenzoporphyrins Related to Phthalocyanines

References

10 Synthesis and Properties of Metalloporphyrins

I. Introduction

II. General Considerations

III. Central Metals of Group Ia (Alkali Metals)

IV. Central Metals of Groups IIa and IIb (Alkaline Earth and Zinc Metals)

V. Central Metals of Groups IIIa, IIIb, and the Lanthanoids

VI. Central Metals of Groups IVa, IVb, Va, and Vb

VII. Central Metals of Groups VIa and VIIa

VIII. Central Metals of Groups VIIIa and Ib

IX. Postscript

References

11 Geochemistry of Porphyrins

I. Introduction

II. Isolation and Fractionation of Geoporphyrins

III. Identification Methods

IV. Treibs' Scheme

V. A Survey of Geoporphyrins: Occurrence and Properties

VI. Diagenetic Reactions of Tetrapyrroles

VII. Concluding Remarks

References

12 Chromatography of Porphyrins and Metalloporphyrins

I. Introduction

II. Porphyrins and Metalloporphyrins

III. Porphyrin and Metalloporphyrin Esters

IV. Synthetic Porphyrins

V. Conclusion

VI. Addendum

References

13 Nonchromatographic Methods of Purification of Porphyrins

I. Introduction

II. Electrophoresis

III. Countercurrent Distribution

IV. Extraction Methods

V. Precipitation and Crystallization

VI. Sublimation

VII. Miscellaneous

VIII. Problems and Future Perspectives

References

Author Index

Subject Index