The Chemistry of Linear Oligopyrroles and Bile Pigments

ISBN-13: 9783709174418 / Angielski / Miękka / 2011 / 621 str.

Heinz Falk

Opis

so easy it seemed Once found, which yet unfound most would have thought Impossible. (John Milton, 1608 -1674) There are essentially two types of books on a scientific subject: in the first one several authors contribute their specialized approaches to parts of the field in question, which then are edited and compiled to yield a comprehensive and authoritative account. In the second type of book a single author tries to pre sent a view from an individual standpoint which might lead to a more balanced and homogeneous source of information. Both kinds have their merits and de ficiencies. I decided to write this book as a monolithic piece of work for several rea sons. Of course, there was the challenge of coping with the many problems of such an undertaking due to the fact that this field has grown tremendously during the last decades. In addition, being heavily involved in linear oligopyr role chemistry for nearly two decades, it seemed worthwile to prepare a more unifying approach. The request of several colleagues from abroad to give an account in English also triggered this endeavor since most of the work of my group has been published in German."

Spis treści

1. Introduction.- 2. Nomenclature.- 3. Occurrence, Formation, and Importance.- 4. Historical Aspects.- 5. Structure and Stereochemistry.- 5.1. General Considerations.- 5.1.1. Definitions.- Constitution.- Tautomerism.- Configuration.- Conformation.- Association.- 5.1.2. Energetics, Interconversions, Interdependencies.- 5.1.3. Methods of Structural Analysis.- Crystalline Materials.- Amorphous Materials.- Solutions.- 5.1.4. Principal Considerations on Structural Aspects of Linear Oligopyrroles.- Bipyrroles.- Bipyrrolylidenes.- Dipyrrins (Pyrromethenes).- Dipyrrinones (Pyrromethenones).- 5,10-Dihydrodipyrrins (Dipyrrylmethanes).- Dihydrodipyrrinones (Dihydropyrromethenones).- Tetrahydrodipyrrinones (Tetrahydropyrromethenones).- Prodigiosenes.- Tripyrrinones.- 1,19-Dioxobilins.- Dihydrobilins: 1,19-Dioxobiladienes-ac.- Dihydrobilins: 1,19-Dioxobiladienes-ab.- Dihydrobilins:1,19-Dioxo-2,3-dihydrobilins.- Tetrahydrobilins: 1,19-Dioxobilenes-b.- Tetrahydrobilins: 1,19-Dioxo-2,3-dihydrobiladienes-ab.- Hexahydrobilins: 1,19-Dioxobilanes.- Hexahydrobilins: Bilanes.- Secocorrins.- 1,19-Dioxo-10-nor-bilins and 1,19-Dioxo-10-nor-biladienes-ac.- Pentapyrrins.- 5.2. Structural Aspects of Linear Dipyrroles.- 5.2.1. Bipyrroles, Bipyrrolylidenes, and Analoga.- 5.2.2. Dipyrrins (Pyrromethenes).- 5.2.3. Dipyrrinones (Pyrromethenones) and Analoga.- 5.2.4. 5,10-Dihydrodipyrrins (Dipyrrylmethanes).- 5.2.5. Dihydrodipyrrinones (Dihydropyrromethenones).- 5.2.6. Tetrahydrodipyrrinones (Tetrahydropyrromethenones).- 5.3. Structural Aspects of Linear Tripyrroles.- 5.3.1. Terpyrroles.- 5.3.2. Prodigiosenes.- 5.3.3. Tripyrrinones and Analoga.- 5.4. Structural Aspects of Linear Tetrapyrroles.- 5.4.1. 1,19-Dioxobilins and Bilins.- 5.4.2. Dihydrobilins: 1,19-Dioxo-2,3-dihydrobilins.- 5.4.3. Dihydrobilins: 1,19-Dioxobiladienes-ac.- 5.4.4. Dihydrobilins: 1,19-Dioxobiladienes-ab.- 5.4.5. Tetrahydrobilins: 1,19-Dioxo-2,3-dihydrobiladienes-ab.- 5.4.6. Tetrahydrobilins: 1,19-Dioxobilenes-b.- 5.4.7. Tetrahydrobilins: Secocorphins.- 5.4.8. Hexa- and Octahydrobilins.- 5.4.9. Secocorrins.- 5.4.10. 1,19-Dioxo-l0-nor- Bilins and Biladienes-ac.- 5.5. Structural Aspects of Linear Oligopyrroles Containing Five or More Rings.- 5.5.1. Pentapyrrins.- 5.5.2. Hexapyrrins and Higher Homologues.- 5.5.3. Polypyrrole.- 6. Synthesis.- 6.1. Principal Considerations.- 6.2. Synthesis of Linear Dipyrroles.- 6.2.1. Bipyrroles, Bipyrrolylidenes, and Analoga.- 6.2.2. Dipyrrins (Pyrromethenes) and Analoga.- 6.2.3. Dipyrrinones (Pyrromethenones) and Analoga.- 6.2.4. 5,10-Dihydrodipyrrins (Dipyrrylmethanes).- 6.2.5. Dihydrodipyrrinones (Dihydropyrromethenones).- 6.2.6. Tetrahydrodipyrrinones (Tetrahydropyrromethenones).- 6.2.7. Miscellaneous Dipyrroles.- 6.3. Synthesis of Linear Tripyrroles.- 6.4. Synthesis of Linear Tetrapyrroles.- 6.4.1. 1,19-Dioxobilins and Bìlins.- 6.4.2. Dihydrobilins: 1,19-Dioxo-2,3-dihydrobilins.- 6.4.3. Dihydrobilins: 1,19-Dioxobiladienes-ac.- 6.4.4. Dihydrobilins: 1,19-Dioxobiladienes-ab.- 6.4.5. Tetrahydrobilins: 1,19-Dioxo-2,3-dihydrobiladienes-ab.- 6.4.6. Tetrahydrobilins: 1,19-Dioxobilenes-b.- 6.4.7. Tetrahydrobilins: Secocorphins.- 6.4.8. Hexahydrobilins and Octahydrobilins.- 6.4.9. Secocorrins.- 6.4.10. 1,19-Dioxo-l0-nor- Bilins and Biladienes-ac.- 6.5. Synthesis of Linear Pentapyrroles and Higher Homologues.- 6.6. Transformations of Functional Groups Attached to Linear Oligopyrroles.- 7. Selected Physical Properties.- 7.1. Crystallization, Melting, Solubility.- 7.2. Light Absorption.- 7.3. Chiroptical Properties.- 7.4. Light Emission.- 7.5. Vibrational Spectroscopy.- 7.6. Nuclear Magnetic Resonance.- 7.7. Mass Spectra.- 8. Reactions.- 8.1. Photochemistry.- 8.2. Protonation — Deprotonation.- 8.3. Coordination (Carrier Mediated Transport).- 8.4. Nucleophilic, Electrophilic, and Radical Reactivity of Linear Oligopyrroles.- 8.5. Substitution Reactions.- 8.6. Addition Reactions.- 8.7. Skeletal Transformations.- 8.8. Reduction — Oxidation.- 8.9. Linear Oligopyrroles as Catalysts.- References.- Author Index.