1. Permanganate ................................................. 1
1.1. Introduction ............................................ 1
1.2. General Procedure for Oxidation of Primary Alcohols to
Carboxylic Acids with Potassium Permanganate ............ 5
1.3. Functional Group and Protecting Group Sensitivity to
Potassium Permanganate .................................. 7
1.4. Side Reactions .......................................... 9
1.5. References ............................................. 10
2. Jones and Other Cr03-Based Oxidations ....................... 13
2.1. Introduction ........................................... 13
Mechanism .............................................. 13
Inverse Addition ....................................... 15
Solvent ................................................ 16
Acidity ................................................ 17
Zhao's Catalytic Cr03 Oxidation ........................ 18
2.2. General Procedure for Oxidation of Primary Alcohols
to Carboxylic Acids with Jones Reagent ................. 19
2.3. Functional Group and Protecting Group Sensitivity
to Jones Oxidation ..................................... 21
2.4. Side Reactions ......................................... 25
2.5. References ............................................. 28
3. Pyridinium Dichromate (PDC) in Dimethylformamide.
The Method of Corey and Schmidt ............................. 33
3.1. Introduction ........................................... 33
3.2. General Procedure for Oxidation of Aliphatic Primary
Alcohols to Carboxylic Acids with Pyridinium
Dichromate in Dimethylformamide. Method of Corey and
Schmidt ................................................ 34
3.3. Functional Group and Protecting Group Sensitivity to
PDC in DMF ............................................. 36
3.4. Side Reactions ......................................... 38
3.5. References ............................................. 39
4. Heyns Oxidation ............................................. 43
4.1. Introduction ........................................... 43
Solvent ................................................ 45
pH ..................................................... 46
Oxygen ................................................. 48
Platinum ............................................... 48
Poisons ................................................ 49
Selectivity ............................................ 50
Application ............................................ 52
4.2. General Procedure for Heyns Oxidation of Primary
Alcohols to Carboxylic Acids ........................... 52
4.3. Functional Group and Protecting Group Sensitivity to
Heyns Oxidation ........................................ 55
4.4. Side Reactions ......................................... 56
4.5. References ............................................. 58
5. Ruthenium Tetroxide and Other Ruthenium Compounds ........... 61
5.1. Introduction ........................................... 61
Procedure of Pappo and Becker .......................... 61
Sharpless' Modification ................................ 62
Mechanism .............................................. 63
Solvent ................................................ 63
Buffering .............................................. 65
Ru04 Source ............................................ 65
Secondary Oxidant ...................................... 66
Ruthenate and Perruthenate Oxidations .................. 66
Application ............................................ 68
5.2. General Procedure for Oxidation of Primary Alcohols
to Carboxylic Acids with Catalytic Ru04 ................ 68
5.3. Functional Group and Protecting Group Sensitivity to
Oxidation with Catalytic Ru04 .......................... 70
5.4. Side Reactions ......................................... 74
5.5. References ............................................. 76
6. TEMPO-Mediated Oxidations ................................... 79
6.1. Introduction ........................................... 79
Mechanism .............................................. 81
Stoichiometric Oxidants ................................ 83
Amino 1-Oxyl Radicals .................................. 83
6.2. Anelli's Oxidation ..................................... 83
Solvent ................................................ 85
Catalyst ............................................... 86
Phase-Transfer Catalyst ................................ 87
pH ..................................................... 87
Selectivity ............................................ 88
6.2.1. General Procedure for Oxidation of Primary
Alcohols to Carboxylic Acids by Anelli's
Oxidation ....................................... 90
6.3. Zhao's Modification of Anelli's Oxidation .............. 93
6.3.1. General Procedure for Oxidation of Primary
Alcohols to Carboxylic Acids by Zhao's
Modification of Anelli's Oxidation .............. 94
6.4. Oxidation of Epp and Widlanski ......................... 96
Mechanism .............................................. 96
Selectivity ............................................ 97
6.4.1. General Procedure for Oxidation of Primary
Alcohols to Carboxylic Acids by the Protocol
of Epp and Widlanski ............................ 98
6.5. Functional Group and Protecting Group Sensitivity
to TEMPO-Mediated Oxidations ........................... 99
6.6. Side Reactions ........................................ 100
6.7. References ............................................ 101
7. Oxidation of Alcohols to Carboxylic Acids via Isolated
Aldehydes .................................................. 105
7.1. Introduction .......................................... 105
7.2. References ............................................ 109
Index ......................................................... 111
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