Free download Oxidation of Alcohols to Aldehydes and Ketones_ A Guide to Current Common Practice by Gabriel Tojo

Authors of:  Oxidation of Alcohols to Aldehydes and Ketones_ A Guide to Current Common Practice by Gabriel Tojo

Gabriel Tojo

Marcos Fernandez

Table of Contents in Oxidation of Alcohols to Aldehydes and Ketones_ A Guide to Current Common Practice by Gabriel Tojo

Here’s the table of contents without the dots and page numbers:

1. Chromium-Based Reagents  

1.1. Introduction  

1.1.1. Jones Reagent  

1.1.2. Sarett and Collins Reagents  

1.1.3. Pyridinium Dichromate (PDC)  

1.1.4. Pyridinium Chlorochromate (PCC)  

1.1.5. Election of Oxidant  

Section 1.1. References  

1.2. Jones Oxidation  

1.2.1. General Procedure for Transformation of Alcohols to Ketones by Jones Oxidation  

1.2.2. Protecting Group Sensitivity to Jones Oxidation  

1.2.3. Functional Group Sensitivity to Jones Oxidation  

1.2.4. In situ Deprotection and Oxidation of Alcohols to Ketones  

1.2.5. Obtention of Aldehydes by Jones Oxidation  

1.2.6. Side Reactions  

Section 1.2. References  

1.3. Collins Oxidation  

1.3.1. General Procedure for Oxidation of Alcohols to Aldehydes and Ketones by Collins Oxidation  

1.3.2. Functional Group and Protecting Group Sensitivity to Collins Oxidation  

1.3.3. Side Reactions  

Section 1.3. References  

1.4. Pyridinium Dichromate (PDC)  

1.4.1. General Procedure for Oxidation of Alcohols to Aldehydes and Ketones with Pyridinium Dichromate (PDC)  

1.4.2. Functional Group and Protecting Group Sensitivity to Oxidation with PDC  

1.4.3. Side Reactions  

Section 1.4. References  

1.5. Pyridinium Chlorochromate (PCC)  

1.5.1. General Procedure for Oxidation of Alcohols to Aldehydes and Ketones with Pyridinium Chlorochromate (PCC)  

1.5.2. Functional Group and Protecting Group Sensitivity to Oxidation with PCC  

1.5.2.1. Protecting Groups  

1.5.2.2. Alkenes  

1.5.2.3. Furan Rings  

1.5.2.4. Tertiary Allylic Alcohols  

1.5.2.5. Secondary Allylic Alcohols  

1.5.2.6. Homoallylic Alcohols  

1.5.2.7. 5,6-Dihydroxyalkenes  

1.5.2.8. 5-Hydroxyalkenes  

1.5.2.9. Epoxides  

1.5.2.10. Lactols  

1.5.2.11. Acetals  

1.5.2.12. 1,2-Diols  

1.5.2.13. 1,4-Diols  

1.5.2.14. 1,5-Diols  

1.5.2.15. Nitrogen-Containing Compounds  

1.5.2.16. Sulfides  

1.5.3. Side Reactions  

1.5.3.1. Oxidative Breakage of a Carbon-Carbon Bond from an Intermediate Chromate Ester  

1.5.3.2. Formation of Conjugated Enones (or Enals) by Eliminations Subsequent to Alcohol Oxidation  

1.5.3.3. Chromate as Leaving-Group and Reactions Induced by the Acidic Nature of PCC  

1.5.3.4. Oxidative Dimerization of Primary Alcohols  

1.5.3.5. Oxidation Products Suffering Subsequent Reactions in Which PCC Plays no Role  

1.5.3.6. Side Reactions in Which Several of the Above Principles Operate  

Section 1.5. References  

1.6. Other Chromium-Based Oxidants  

1.6.1. Chromic Acid  

1.6.2. Chromium Trioxide and Pyridine  

1.6.3. Dichromate Salts  

1.6.4. Halochromate Salts  

1.6.5. Oxidations Using Catalytic Chromium Compounds  

1.6.6. Miscellanea  

Section 1.6. References  

2. Activated Dimethyl Sulfoxide  

2.1. Introduction  

2.1.1. A Proposal for Nomenclature of Reactions Involving Activated DMSO  

Section 2.1. References  

2.2. PWtzner–MoVatt Oxidation (Carbodiimide-Mediated MoVatt Oxidation)  

2.2.1. General Procedure for Oxidation of Alcohols by PWtzner–MoVatt Method  

2.2.2. Functional Group and Protecting Group Sensitivity to PWtzner–MoVatt Oxidation  

2.2.3. Side Reactions  

Section 2.2. References  

2.3. Albright–Goldman Oxidation (Acetic Anhydride-Mediated MoVatt Oxidation)  

2.3.1. General Procedure for Oxidation of Alcohols by Albright–Goldman Method  

2.3.2. Functional Group and Protecting Group Sensitivity to Albright–Goldman Oxidation  

2.3.3. Side Reactions  

Section 2.3. References  

2.4. Albright–Onodera Oxidation (Phosphorous Pentoxide-Mediated MoVatt Oxidation)  

2.4.1. General Procedure Albright–Onodera Oxidation using the Taber Modification  

2.4.2. Functional Group and Protecting Group Sensitivity to Albright–Onodera Oxidation  

Section 2.4. References  

2.5. Parikh–Doering Oxidation (Sulfur Trioxide-Mediated MoVatt Oxidation)  

2.5.1. General Procedure for Parikh–Doering Oxidation  

2.5.2. Functional Group and Protecting Group Sensitivity to Parikh–Doering Oxidation  

2.5.3. Side Reactions  

Section 2.5. References  

2.6. Omura–Sharma–Swern Oxidation (TFAA-Mediated MoVatt Oxidation)  

2.6.1. General Procedure (Procedure A) for Oxidation of Alcohols with Omura–Sharma–Swern Method  

2.6.2. Functional Group and Protecting Group Sensitivity to Omura–Sharma–Swern Oxidation  

2.6.3. Side Reactions  

Section 2.6. References  

2.7. Swern Oxidation (Oxalyl Chloride-Mediated MoVatt Oxidation)  

2.7.1. General Procedure for Oxidation of Alcohols using Swern Oxidation  

2.7.2. Functional Group and Protecting Group Sensitivity to Swern Oxidation  

2.7.3. Reactions Performed in situ after a Swern Oxidation  

2.7.4. Side Reactions  

2.7.4.1. Activated DMSO as a Source of Electrophilic Chlorine  

2.7.4.2. Activated DMSO as a Source of Electrophilic Sulfur  

2.7.4.3. Transformation of Alcohols into Chlorides  

2.7.4.4. Methylthiomethylation  

2.7.4.5. Base-induced Reactions  

2.7.4.6. Acid-induced Reactions  

2.7.4.7. Formation of Lactones from Diols  

Section 2.7. References  

2.8. Corey–Kim Oxidation  

2.8.1. General Procedure for Oxidation of Alcohols using the Corey–Kim Method  

2.8.2. Functional Group and Protecting Group Sensitivity to Corey–Kim Oxidations  

2.8.3. Side Reactions  

Section 2.8. References  

2.9. Other Alcohol Oxidations Using Activated DMSO  

Section 2.9. References  

3. Hypervalent Iodine Compounds  

3.1. Introduction  

Section 3.1. References  

3.2. Dess–Martin Periodinane  

3.2.1. General Procedure for Oxidation of Alcohols using Dess–Martin Periodinane  

3.2.2. Functional Group and Protecting Group Sensitivity to Dess–Martin Oxidation  

3.2.3. Reactions Performed in situ During a Dess–Martin Oxidation  

3.2.4. Side Reactions  

Section 3.2. References  

3.3. o-Iodoxybenzoic Acid (IBX)  

3.3.1. General Procedure for Oxidation of Alcohols with IBX  

3.3.2. Functional Group and Protecting Group Sensitivity to Oxidations with IBX  

3.3.3. Reactions Performed in situ During Oxidation with IBX  

Section 3.3. References  

3.3.4. Side Reactions  

3.4. Other Hypervalent Iodine Compounds Used for Oxidation of Alcohols  

Section 3.4. References  

4. Ruthenium-Based Oxidations  

4.1. Introduction

4.1.1. Ruthenium Tetroxide  

4.1.2. Tetrapropylammonium Perruthenate (TPAP)  

4.1.3. Potassium Permanganate  

Section 4.1. References  

4.2. Ruthenium Tetroxide (RuO4) Oxidations  

4.2.1. General Procedure for Oxidation of Alcohols with Ruthenium Tetroxide (RuO4)  

4.2.2. Functional Group and Protecting Group Sensitivity to Oxidation with RuO4  

4.2.3. Side Reactions  

Section 4.2. References  

4.3. TPAP Oxidation (Ley-Griffith Oxidation)  

4.3.1. General Procedure for TPAP-Mediated Oxidation of Alcohols to Aldehydes or Ketones  

4.3.2. Functional Group and Protecting Group Sensitivity to TPAP Oxidation  

4.3.3. Side Reactions  

Section 4.3. References  

5. Miscellaneous Methods  

5.1. Introduction  

Section 5.1. References  

5.2. TEMPO Oxidation  

5.2.1. General Procedure for TEMPO-Mediated Oxidation of Alcohols  

5.2.2. Functional Group and Protecting Group Sensitivity to TEMPO Oxidation  

5.2.3. Side Reactions  

Section 5.2. References  

5.3. DMPU-Catalyzed Oxidation  

5.3.1. General Procedure for DMPU-Catalyzed Oxidation of Alcohols  

5.3.2. Functional Group and Protecting Group Sensitivity to DMPU-Catalyzed Oxidation  

5.3.3. Side Reactions  

Section 5.3. References  

5.4. Nonmetallic Oxygen-Transfer Agents  

Section 5.4. References  

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