The article contains sections titled: 1. Introduction and History 2. Methods of Production 2.1. Anthraquinonesulfonic Acids 2.2. Alkyl‐ and Arylanthraquinones 2.3. Haloanthraquinones 2.4. Nitroanthraquinones 2.5. Aminoanthraquinones 2.5.1. General Aspects 2.5.1.1. Replacement Reactions 2.5.1.2. Modifications of the Amino Functions 2.5.1.3. Substitutions on the Aminoanthraquinone Nucleus 2.5.2. Individual Aminoanthraquinones 2.5.3. Diazotization of Aminoanthraquinones 2.6. Hydroxyanthraquinones, Alkoxy‐ and Aryloxyanthraquinones 2.6.1. General Aspects 2.6.1.1. Synthesis of the Nucleus 2.6.1.2. Replacement Reactions 2.6.1.3. Conversions of the Hydroxy Group 2.6.1.4. Substitutions on the Hydroxyanthraquinone Nucleus 2.6.2. Individual Hydroxyanthraquinones 2.7. Mercaptoanthraquinones 2.7.1. General Aspects 2.7.2. Individual Mercapto Compounds and Thioethers 2.8. Anthraquinonesulfones 2.9. Anthraquinone Aldehydes and Their Derivatives 2.10. Anthraquinonecarboxylic Acids and Carboxylic Acid Derivatives 2.10.1. General Aspects 2.10.2. Individual Anthraquinonecarboxylic Acids 2.11. Anthraquinone Derivatives with Condensed Rings 2.11.1. Anthraquinone Derivatives Containing Imidazole, Oxazole, and Thiazole Rings 2.11.2. Anthraquinonecarbazole Derivatives 2.11.3. Anthraquinone Derivatives with Acridone Substructure (Phthaloylacridones) 2.11.4. Anthraquinone Derivatives with Phenazine Substructure 2.12. Anthraquinone Derivatives with Meso Rings (1,9‐Cyclo‐10‐anthrones) 2.12.1. Benzanthrone and Its Derivatives 2.12.2. Pyrazolanthrone and Its Derivatives 2.12.3. 1,9‐Anthrapyrimidine and Its Derivatives (1,9( N ‐)‐Pyrimidinoanthrone‐10) 2.12.4. 1,9‐Anthrapyridone and Its Derivatives 2.12.5. Dibenzpyrenequinones 2.12.6. Anthanthrones 2.12.7. Pyranthrone and Flavanthrone 2.12.8. Violanthrone and Isoviolanthrone 2.12.9. Acedianthrone 3. Dye Classes 3.1. Neutral Dyes 3.1.1. Disperse Dyes 3.1.1.1. Dyes for Polyester Fibers 3.1.1.2. Dyes for Cellulose Ester and Synthetic Polyamide Fibers 3.1.1.3. Transfer Dyes 3.1.1.4. Dyes for Cotton ‐ Polyester Fabrics 3.1.2. Dyes Soluble in Organic Solvents 3.1.3. Vat Dyes 3.1.4. Pigments 3.2. Anionic Dyes 3.2.1. Acid Dyes 3.2.2. Direct Dyes 3.2.3. Reactive Dyes 3.3. Cationic Dyes
ortho-(Acy1amino)halogenarornaten 1 und 3 kiinnen ohne Aktivierung durch Elektronenakzeptor-Substituenten mit metallischem Kupfer unter milden Bedingungen in guten Ausbeuten zu symmetrischen Biarylverbindungen 2 und 4 kondensiert werden. Grundsatzlich ist auch die Synthese unsymmetrischer Biarylverbindungen moglich. Vermutlich greift die Acylaminogruppe direkt unter Bildung einer intermediaren organischen Kupferverbindung in den Reaktionsablauf ein. Ullmann Reactions of ortho-(Acylamino)halogenoarenes * *)orrho-(Acy1amino)halogenoarenes 1 and 3 are condensed in presence of metallic copper under mild conditions to give symmetrical biaryl compounds 2 and 4 in good yields. In principle the synthesis of unsymmetrical biaryl compounds is also possible. The acylamino group probably participates directly by forming an organic copper intermediate.Die Ullmann-Reaktion I), d. h. die Synthese von Biarylderivaten durch Kondensation aromatischer Halogenverbindungen mit metallischen Agentien, vor allem Kupferpulver, gehort zum klassischen Kepertoire der organischen ,,Namen-Reaktionen" : Ar-Hal + Ar'-Hal -cu2Ha,z +2cu -+ Ar-Ar'
Die Titelverbindun‐ gen (I) bzw. (IV) können ohne Aktivierung durch Elektronenakzeptor‐Substituenten mit metallischem Cu unter milden Bedingungen zu symm. Biarylverbindungen (II) bzw. (V) kondensiert werden (die Verbindungen (III) werden analog dargestellt).
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