Chromium Oxidations in Organic Chemistry

I. Introduction.- 1. The Oxidation States of Chromium.- 2. The Chemistry of Chromium(VI).- 3. Chromium(VI) as Oxidant in Organic Chemistry.- References of Chapter I.- II. Oxidation of Carbon-Hydrogen Bonds.- A. Oxidation of Alkanes.- 1. Oxidation of Alkanes With Chromic Acid in Acetic Acid.- 2. Oxidation of Alkanes With Chromic Acid inAqueous Sulphuric Acid.- 3. Oxidation of Alkanes With Chromyl Chloride.- 4. Mechanism of Oxidation of Alkanes.- B. Oxidation of Arylalkanes (Benzylie Oxidation).- 1. Oxidation of Arylalkanes With Chromic Acid in an Acidic medium.- 2. Oxidation of Arylalkanes With Aqueous Sodium Dichromate.- 3. Oxidation of Arylalkanes With Chromyl Chloride (Etard Reaction).- 4. Mechanism of Benzylic Oxidation.- C. Allylic Oxidation.- 1. Allylic Oxidation of Olefins With Chromium(VI) in Acetic Acid and Acetic Anhydride.- 2. Allylic Oxidation With Chromium Trioxide-Heterocyclic Bases Addition Compounds.- 3. Allylic Oxidation With Tert-butyl-chrornate.- 4. Mechanism of Allylic Oxidation.- References of Chapter II.- III. Oxidation of Carbon-Carbon Double Bonds.- A. Oxidation of Alkenes.- 1. Oxidation of Alkenes With Chromium Trioxide in Acetic Anhydride or Acetic Acid.- 2. Oxidation of Alkenes With Chromic Acid in Aqueous Sulphuric Acid.- 3. Mechanism of Alkene Oxidation With Chromic Acid.- 4. Oxidation of Alkenes With Chromyl Chloride.- 5. Mechanism of Alkene Oxidation With Chromyl Chloride.- 6. Oxidation of Alkenes With Silver Chromate-Iodine.- B. Oxidation of Enol-Derivatives 901. Oxidation of Enol-Ethers With Pyridinium Chlorochromate.- 2. Oxidation of O-Silylated Enolates With Chromyl Chloride.- C. Ring Oxidation of Aromatic Compounds.- 1. Oxidation of Polynuclear Arenes With Chromium(VI) Under Acidic Conditions.- 2. Oxidation of Phenols and Aromatic Amines With Chromium(VI) Under Acidic Conditions.- 3. Oxidation of Phenols With Chromyl Chloride.- 4. Oxidation of Hydroquinone Silyl Ethers With Pyridinium Chlorochromate.- 5. Oxidation of Ortho-Allylphenols With Tetraalkylammonium Dichrornate.- 6. Oxidation of Some Aromatic Heterocyclic Compounds With Chromium(VI).- References of Chapter III.- IV. Oxidation of Alcohols.- A. Oxidation of Alcohols by Chromium(VI) Under Acidic Conditions.- 1. Oxidation of Alcohols With Chromic Acid in Aqueous Sulfuric Acid.- 2. Oxidation of Alcohols With Chromic Acid in Acetic Acid or Aqueous Acetic Acid.- 3. Oxidation of Alcohols With Chromic Acid in Aqueous Sulfuric Acid and Acetone (Jones’Reagent).- 4. Oxidation of Alcohols With Chromic Acid in Dimethylformamide or Dimethylsulphoxide Containing Sulphuric Acid.- 5. Oxidation of Alcohols With Chromic Acid in Two-phase systems.- B. Oxidation of Alcohols With Compounds of Chromium(VI) and Heterocyclic Bases.- 1. Oxidation of Alcohols With Chromium Trioxide-(Pyridine)2 Complex.- 2. Oxidation of Alcohols With Pyridinium Dichromate.- 3. Oxidation of Alcohols With Pyridinium Chlorochromate (PCC).- 4. Oxidation of Alcohols With Pyridinium Fluorochromate.- 5. Oxidation of Alcohols With Chromium Trioxide-3,5-Dimethylpyrazole Complex.- 6. Oxidation of Alcohols With 2,2?-Bipyridinium Chlorochromate.- 7. Oxidation of Benzylic and Ally lic Alcohols With 4-(Dimethylamino)pyridinium Chlorochromate (DMAP • HCrO3Cl).- 8. Oxidation of Alcohols With Chromium(V) Reagents.- C. Oxidation of Alcohols With Chromium(VI) Under Neutral Conditions.- 1. Oxidation of Alcohols With Di-tert-butylchromate (TBC).- 2. Oxidation of Alcohols With Chromium Trioxide in Hexamethylphosphoramide.- 3. Oxidation of Alcohols With Tetraalkylammonium Chromates in Apolar Solvents.- D. Oxidation of Alcohols With Supported Chromium(VI) Reagents.- 1. Oxidation of Alcohols With Chromium(VI) Reagents Supported on Organic Polymers.- 2. Oxidation of Alcohols With Chromium(VI) Reagents Adsorbed or Dispersed on Inorganic Support.- E. Mechanism of Oxidation of Alcohols.- F. Effect of the Structure and Stereochemistry of Secondary Alcohols on the Rate of Oxidation.- References of Chapter IV.- V. Oxidation of Aldehydes and Ketones.- A. Oxidation of Aldehydes.- 1. Oxidation of Aldehydes With Chromic Acid Under Acidic Conditions.- 2. Oxidation of Aldehydes With Pyridinium Chlorochromate and Pyridinium Dichrornate.- 3. Oxidation of Aldehydes With Chromium(V) Reagents.- 4. Mechanism of Aldehyde Oxidation.- B. Oxidation of Ketones.- 1. Oxidation of Ketones With Chromic Acid Under Acidic Conditions.- 2. Mechanism of Ketone Oxidation.- References of Chapter V.- VI. Oxidation of Carbon-Metal Bonds.- A. Oxidation of Organoboron Compounds.- 1. Oxidation of Organoboranes With Chromic Acid Under Acidic Conditions.- 2. Oxidation of Organoboranes With Pyridinium Chlorochromate.- 3. Oxidation of Trialkylborates With Pyridinium Chlorochromate.- 4. Oxidation of 1,1- and 1,2-diorganoboranes With Chromium Trioxide-(Pyridine)2.- B. Oxidation of Organotin Compounds.- 1. Oxidation of Organotin Compounds With Chromium Trioxide-(Pyridine)2 and Pyridinium Chlorochromate.- References of Chapter VI.- VII. Oxidation of Halides, Ethers, Acetals, Sulphides, and Some Nitrogen Containing Compounds.- A. Oxidation of Alkyl Halides.- B. Oxidation of Ethers.- C. Oxidation of Acetals.- D. Oxidation of Sulphides.- E. Oxidation of Alkyl Aryl Amines.- F. Oxidation of Oximes.- G. Oxidation of Hydroxylamine.- References of Chapter VII.- VIII. Some Remarks on Selectivity and Synthetic Use of Chromium (VI) Oxidation.- A. Oxidation of Carbon-Hydrogen Bond.- 1. Alkanes.- 2. Arylalkanes.- 3. Allylic Oxidation.- B. Oxidation of Carbon-Carbon Double Bonds.- 1. Oxidation of Alkenes.- 2. Oxidation of Enol Derivatives.- C. Ring Oxidation of Aromatic Compounds.- D. Oxidation of Alcohols.- E. Oxidation of Aldehydes and Ketones.- F. Oxidation of Carbon-Metal Bonds.