Synthesis of aldehydes, ketones and quinones , Hive Chemistry Discourse


		Nicodem (Hive Bee) 11-06-04 16:14 No 540029				Synthesis of aldehydes, ketones and quinones (Rated as: excellent)
						Here is a review of all literature and known methods for the synthesis of aldehydes, ketones and quinones until the year 1953 when the book was written. You will find it is a nice source of ideas and old references. Chapters 9, 10 and 11 from: Romeo B. Wagner & Harry D. Zook. Synthetic organic chemistry. (1953) New York: John Wiley & Sons, inc. ^1.9MB The methods described ^{(keywords for the TFSE)}: Aldehydes Formylation with Carbon Monoxide (Gattermann-Koch) Formylation with Cyano Compounds (Gattermann) Formylation with N-Methylformanilide Formylation of Phenols with Chloroform (ReimerTiemann) Formylation of Phenols (or Amines) with Hexamine (Duff) Hydroformylation of Unsaturated Compounds Formylation of Ketones with Formic Esters Interaction of Halomethyl Compounds and Hexamine (Sommelet) Interaction of Benzyl Halides and Sodium 2-Propanenitronate Decomposition of Arylsulfonohydrazides Cleavage of Schiff Bases Hydrolysis of gem-Dihalides Interaction of Pyridinium Salts and p-Nitrosodimethylaniline Hydrolysis of 2-Alkoxy-3.4-dihydro-1.2-pyrans Hydrolysis of Aldehyde Derivatives Oxidation of Aromatic Side Chains Oxidation of Olefinic Compounds Oxidation of Methyl Ketones by Selenium Dioxide Oxidation of Primary Alcohols Dehydrogenation of Primary Alcohols Oxidative Cleavage of Glycols Selective Reduction of Olefinic Aldehydes Reduction of Acyl Chlorides (Rosenmund) Reduction of Thiol Esters Reduction of Nitriles (Stephen) Interaction of Grignard Reagents and Orthoformic Esters Interaction of Grignard Reagents and Ethoxymethyleneaniline Decomposition of Glycol Monoalkyl Ethers Thermal Uecomposition of Acids Decomposition of a-Hy&oxy Acids Decarborylation of a-Keto Acids Decarboxylation of Glycidic Acids Hydrolysis of Olefin Dibromides Degradation of Acid Amides and Azides Acid Treatment of Primary Acznitroparaffins Isomerization of Unsaturated Alcohols Condensation of Aromatic Hydrocarbons with Chloral Fomylation of Acetylenes Ketones Acylation of Hydrocarbons (Friedel-Crafts) Oxidation of Secondary Alcohols Oxidation of Alcohols by Ketones (Oppenauer) Catalytic Dehydrogenation of Secondary Alcohols Oxidation of Olefinic Compounds (Ozonolysis) Oxidation of Methylene Groups Cleavage of beta-Keto Esters Decarboxylation of Acylmalonic Acids Thermal Decarboxylation of Acids Interaction of Grignard Reagents and Nitriles Interaction of Organometallic Reagents and Anhydrides Interaction of Organometallic Reagents and Acyl Chlorides Interaction of Grignard Reagents and Amides Interaction of Grignard Reagents and olefinic Ketones Interaction of Grignard Reagents and Halo Ketones Interaction of Organometallic Reagents and Esters Interaction of Organometallic Reagents and Salts of Carboxylic Acids Hydrolysis of Ketone Derivatives Selective Reduction of alpha, beta-Olefinic Ketones Partial Reduction of Phenols Alkylation of Ketones Interaction of Diazomethane and Carbonyl Compounds Catalytic Hydration of Acetylenic Compounds Dehydration and Rearrangement of alpha-Diols Decomposition of Glycol Monoalkyl Ethers Diketones by Acylation of Ketones alpha, beta-olefinic Ketones from Acetylenic Carbinols Olefinic Ketones from Alkenyl Esters of beta-Keto Acids Cyclopentenones from Lactones alpha-Halo Ketones from Acyl Chlorides and Olefins alpha-Halo Ketones from Alkenyl Esters Hydroxy Ketones from Phenolic Esters (Fries) alpha-Keto Acids from Azlactones beta-Keto Esters by Condensation of Esters beta-Keto Esters by Selective Cleavage of alpha, alpha-Diacyl Esters beta-Keto Esters by Alkylation of beta-Keto Esters beta-Keto Esters from Ethyl t-Butyl Acylmalonic Esters beta-Keto Esters by Acylation of Ester Enolates beta-Keto Nitriles by Acylation of Nitriles Hydrogenolysis of 1, 3 Diketones Acid Treatment of Aciniuoparaffins Pyrolysis of Glycidic Acids Rearrangement of alpha-Bromo Azides Degradation of Disubstituted Glycolic Acids Hydrolysis of gem-Dihalides Isomerization of Vinyl Carbinols Condensation of Furans with Unsaturated Ketones Condensation of Anhydrides Acylation of Certain Heterocyclic compounds Addition of Aldehydes to Olefins Interaction of Hydriodic Acid and Diazo Ketones delta-Diketones from Substituted Furans alpha-Diketones by Oxidation of Aryl Acetylenes gamma-Diketones from Ketones Olefinic Ketones from Hydrocarbons and Carbon Monoxide alpha, beta-Olefinic Ketones from Diketene and Aldehydes beta-Keto Esters by the Reformatsky Reaction Hydrolysis of beta-Iminonitriles Quinones Oxidation of Aromatic Hydrocarbons Oxidation of Phenols, Aminophenols, and Aryl Diamines Oxidation of 2-Hydroxy-1,4aaphthoquinones Alkylation of Quinones Quinones by Ring Closure Is anybee interested in any other particular chemical group? “The real drug-problem is that we need more and better drugs.” – J. Ott



		Nicodem (Hive Bee) 11-08-04 11:47 No 540394				Synthesis of amines&imines&aziridines&hydrazines (Rated as: excellent)
						I kind of forgot that the most important group is the amine group, so here it is. Again, like already explained in the post above, all the methods until the year 1953. With a bonus included (imines&aziridines and hydrazines). Chapters 24, 25 and 26 from: Romeo B. Wagner & Harry D. Zook. Synthetic organic chemistry. (1953) New York: John Wiley & Sons, inc. ^1.4MB The methods described ^{(keywords for the TFSE)}: Amines Reduction of Nitro Compounds Reduction of Oximes Reduction of Nitriles Reduction of Amides Reduction of Schiff Bases Reduction of Aromatic Amines Reductive Alkylation (or Reductive Amination) Reductive Alkylation of Amines (Leuckart) Reductive Cleavage of Azo Compounds Catalytic Debenzylation of N-Benzyldialkylamines Ammonolysis of Halogen Compounds Alkylation of Amines Interaction of Hexarnine and Halogen Compounds Replacement of Hydroxyl Groups by Amino Groups Amination of Aromatic Nuclei Rearrangement of N-Alkylanilines Amination of Cyclic Imines Amination of Oxides Amination of Unsaturated Compounds Aminome thy lation (Mannich) Aminomethylation of Alcohols Degradation of Amides (Hofmann) Degradation of Acyl Azides (Curtius) Degradation of Hydroxamic Acids (Lossen) Interaction of Hydrazoic Acid and Carbonyl Compounds (Schmidt) Hydrolysis of Isocyanates, Isothiocyanates, Urethanes, and Ureas Hydrolysis of N-Substituted Amides Hydrolysis of NSubstituted Phthalimides (Gabriel) Hydrolysis of Nitrosoanilines Hydrolysis of Quaternary Imine Salts Hydrolysis of Cyanamides Ring Dehydrogenation Condensation of Grignard Reagents and 0-Methylhydroxylamine Addition of Grignard Reagents to Schiff Bases Interaction of Grignard Reagents and Halo Amines Reduction of Unsaturated Amines Interaction of Sodium Amide and Halogen Compounds Rearrangement of Hydrazobenzenes Interaction of Amines and P-Keto Esters Condensation of Unsaturated Amines and Aromatic Compounds Imines ^{(actually it's mostly on aziridines-due to old nomenclature)} Condensation of Carbonyl Compounds with Amines Cyclization of beta-Amino Alcohols Action of Grignard Reagents on Oximes Action of Grignard Reagents on Nitriles beta-Iminonitriles by Condensation of Nitriles Ethylene Imino Ketones by the Action of Amines on alpha, beta-Dibromo Ketones Hydrazines Alkylation of Hydrazines Interaction of Amines and Hydroxylamine-O-Sulfonic Acid Reduction of Diazonium Compounds Reduction of Nitrosoamines Reduction of Azo Compounds Action of Grignard Reagents on Diazomethane Reductive Hydrazination of Carbonyl Compounds Addition of Grignard Reagents to Dialkyl-alkylidenhydrazones Once more, I accept suggestions for which other chemical group would be good to have it scanned (if there is any interest at all). “The real drug-problem is that we need more and better drugs.” – J. Ott