Synthesis of aldehydes, ketones and quinones

[Nicodem]

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.

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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?

[Nicodem]

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 ).