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e-Book: THE NITRO GROUP ORGANIC SYNTHESIS
« on: September 20, 2004, 10:41:00 AM »
THE NITRO GROUP IN ORGANIC SYNTHESIS

Noboru Ono
 2001



1. Introduction 1

2. Preparation of Nitro Compounds 3

2.1 Nitration of Hydrocarbons / 3
2.2 Synthesis of Nitro Compounds by Oxidation / 20

3. The Nitro-Aldol (Henry) Reaction 30

3.1 Preparation of ?-Nitro Alcohols / 31
3.2 Derivatives from ?-Nitro Alcohols / 38
3.3 Stereoselective Henry Reactions and Applications to Organic Synthesis / 51

4. Michael Addition 70

4.1 Addition to Nitroalkenes / 70
4.2 Addition and Elimination Reaction of ?-Heterosubstituted Nitroalkenes / 100
4.3 Michael Addition of Nitroalkanes / 103
4.4 Asymmetric Michael Addition / 115

5. Alkylation, Acylation, and Halogenation of Nitro Compounds 126

5.1 Alkylation of Nitro Compounds / 126
5.2 Acylation of Nitroalkanes / 128
5.3 Ring Cleavage of Cyclic ?-Nitro Ketones (Retro-Acylation) / 131
5.4 Alkylation of Nitro Compounds via Alkyl Radicals / 133
5.5 Alkylation of Nitro Compounds Using Transition Metal Catalysis / 138
5.6 Arylation of Nitro Compounds / 147
5.7 Introduction of Heteroatoms to Nitroalkanes / 149

6 . Conversion of Nitro Compounds into Other Compounds 159

6.1 Nef Reaction (Aldehydes, Ketones, and Carboxylic Acids) / 159
6.2 Nitrile Oxides and Nitriles / 167
6.3 Reduction of Nitro Compounds into Amines / 170

7. Substitution and Elimination of NO2 in R–NO2 182

7.1 R–Nu from R–NO2 / 182
7.2 R–H from R–NO2 / 193
7.3 Alkenes from R–NO2 / 218

8. Cycloaddition Chemistry of Nitro Compounds 231

8.1 Diels-Alder Reactions / 231
8.2 1,3-Dipolar Cycloaddition / 249
8.3 Nitroalkenes as Heterodienes in Tandem [4+2]/[3+2] Cycloaddition / 274

9. Nucleophilic Aromatic Displacement 302

9.1 SNAr / 302
9.2 Nucleophilic Aromatic Substitution of Hydrogen (NASH) / 309

10. Synthesis of Heterocyclic Compounds 325

10.1 Pyrroles / 325
10.2 Synthesis of Indoles / 338
10.3 Synthesis of Other Nitrogen Heterocycles / 346

Index 365