Porphyrin-based photosensitizers for use in photodynamic therapy

Metal Complexes as Photo- and Radiosensitizers

Aromaticity as a cornerstone of heterocyclic chemistry.

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Metal-Assisted Cycloaddition Reactions in Organotransition Metal Chemistry

The Tautomerism of Heterocycles: Five-membered Rings with Two or More Heteroatoms

Publisher Summary An increasing number of porphinoid macrocyclic pigments have been found to be related to important biochemical processes. As a result, much of the pertinent chemistry has been thoroughly studied in the chapter. It also discusses the biochemical implications of hydroporphyrins. Porphyrin is generally regarded as a very stable aromatic system. The chapter provides a convincing explanation of its aromaticity. The connection of this problem to the properties of hydroporphyrins is obvious. As a consequence, some aspects of porphyrin chemistry are included. The chemistry of porphyrins is well documented and chlorophylls and bacteriochlorophylls have been reviewed extensively in the chapter. The chemistry of hydroporphyrins has been investigated so far mainly in view of biochemical problems. Only small amounts of hydroporphyrins, especially those with selected substitutions patterns as, for example, parent compounds, are accessible by the routes described. The progress in biochemistry as well as in essential chemical and physicochemical investigations thus strongly depends on developments in the synthetic field.

Hydrogenated porphyrin derivatives: hydroporphyrins

1. Introduction.- 1.1. Ring-Chain Isomeric Interconversions. General Considerations.- 1.2. Tautomerism or Isomerism? System Mobility and Equilibrium Position.- 1.3. Methods of Investigation of Ring-Chain Addition Tautomerism.- 1.3.1. Chemical Methods.- 1.3.2. Visible and UV Spectroscopy.- 1.3.3. IR Spectroscopy.- 1.3.4. Nuclear Magnetic Resonance.- 1.3.5. Mass Spectrometry.- 1.3.6. X-Ray Diffraction Analysis.- 1.3.7. Polarography.- 1.3.8. Other Physical Methods.- References.- 2. Intramolecular Reversible Addition Reactions to the C=O Group.- 2.1. Aldehydo and Keto-carboxylic Acids and Their Derivatives Modified at the Carboxylic Group.- 2.1.1. Aldehydo- and Keto-carboxylic Acids.- 2.1.2. Acyl Chlorides.- 2.1.3. Amides, Hydrazides, and Amidines.- 2.1.4. Esters.- 2.1.5. Mixed Anhydrides.- 2.2. Hydroxy Aldehydes and Ketones and Related Compounds.- 2.2.1. Derivatives Containing a Hydroxy Group at Carbon (C-OH).- 2.2.2. Derivatives Containing a Hydroxy Group at Nitrogen (N-OH).- 2.3. Amino Aldehydes and Ketones and Related Compounds.- 2.3.1. Covalent Hydration of Nitrogen-Containing Heterocycles.- 2.3.2. Derivatives Containing Amino Groups at sp3-, Aromatic, and sp2-Carbon Atoms.- 2.3.3. Urea and Thiourea Derivatives.- 2.3.4. Dithiocarbamates.- 2.3.5. Sulfonamides and Sulfinamides.- 2.3.6. Pyridones.- 2.3.7. 1,3-Diazaheterocycles.- 2.3.8. Triazenes.- 2.3.9. Miscellaneous.- 2.4. Intramolecular Migration of O-, N-, and S-Acyl Groups.- 2.5. Oxa-, Aza-, and Thiacyclols.- 2.6. Mercapto Aldehydes and Ketones and Related Compounds.- 2.7. Intramolecular Addition of C-H Groups.- References.- 3. Intramolecular Reversible Addition Reactions to the C=N Group.- 3.1. OH-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 3.1.1. N-(Hydroxyalkyl) and N-(hydroxyaryl) imines.- 3.1.2. N-Hydroxyalkylhydrazones.- 3.1.3. Hydroxyalkyl and Hydroxyiminoalkyl Nitrones.- 3.1.4. Imines, Hydrazones, and Oximes of Hydroxyaldehydes and Hydroxyketones.- 3.1.5. Imines of Ketocarboxylic Acids.- 3.1.6. Fused Systems.- 3.2. N-H-Derivatives of Imines, Hydrazones, Oximes, and Nitrones.- 3.2.1. N-Aminoalkylimines.- 3.2.2. N-Aminoalkyl and N-Aminoacyl Hydrazones and Related Compounds.- 3.2.3. 2-Benzimidoyl-benzamides and -benzenesulfonamides.- 3.2.4. N-(2- and 3-Hydroxyiminoalkyl)nitrones.- 3.2.5. Fused Systems.- 3.3. S-H-Derivatives of Imines and Hydrazones.- 3.4. Miscellaneous.- References.- 4. Intramolecular Reversible Addition Reactions to Other Groups.- 4.1. Addition to the C?N Group.- 4.2. Addition to C=C and C?C Groups.- 4.3. Addition to the P=O Group.- 4.4. Addition to the P=N Group.- 4.5. Addition to the S=O Group.- 4.6. Addition to the Se=O Group.- 4.7. Addition to the I=O Group.- References.- 5. Generalizations Concerning the Influence of Structural and External Factors on the Relative Stability of Ring and Chain Isomers.- 5.1. Structural Influences.- 5.1.1. Electronic Effects of Substituents at Interacting Groups.- 5.1.2. Steric Effects of Substituents at Interacting Groups.- 5.1.3. Structure of the Connecting Link.- 5.1.4. Steric Effects of the Substituents at the Connecting Link.- 5.1.5. Intramolecular Hydrogen Bonds.- 5.2. Influence of External Factors.- References.

Ring-chain tautomerism

γ-Ketoamide sind Primarprodukte der Umsetzung von Imiden mit Grignard-Reagentien. Sie konnen in zwei tautomeren Formen vorliegen, die im folgenden mit »K« und »R« bezeichnet werden.

Zur Ring‐Ketten‐Tautomerie der γ‐Ketoamide

1-Amino-pyrrole 1, deren Synthese beschrieben wird, reagieren mit 1.4-Dioxoverbindungen zu Bipyrrylen-(1.1′) 9 und 6H-3a.4-Diaza-azulenen 10.

Cyclische Verbindungen mit Heterobrückenatomen, V. Zur Chemie der 1-Amino-pyrrole

Publisher Summary Cyclazine refers to a conjugated, unsaturated cyclic molecule held planar by three covalent bonds to an internal nitrogen atom. With regard to nomenclature, the various possible cyclazines having rings of different sizes or different points of attachment to nitrogen can be distinguished by adding numbers in brackets, which indicate the number of atoms between the points of attachment to nitrogen. The chapter considers substitution of the peripheral carbon atoms of the cyclazines by heteroatoms, such as nitrogen and sulfur, according to the replacement nomenclature system. The chapter also describes the methods of synthesis of these cyclazine compounds and exhibits how the chemistry of cyclazines has stimulated discussion on theories of condensed Π -systems. The chapter also includes hydrazine and imino-bridged annulenes with internal nitrogen atoms coplanar with the peripheral atoms of the system. It is possible to deduce the properties of heterobridged annulenes from the peripheral Π -system even when the heteroatoms are coplanar with the atoms in the perimeter.

Wilhelm Flitsch

Papers

Hydrogenated porphyrin derivatives: hydroporphyrins

Ring-chain tautomerism

Zur Ring‐Ketten‐Tautomerie der γ‐Ketoamide

Cyclische Verbindungen mit Heterobrückenatomen, V. Zur Chemie der 1-Amino-pyrrole

Cyclazines and Related N-Bridged Annulenes