Displacement of Aliphatic Nitro Groups by Carbon and Heteroatom Nucleophiles

This article reviews novel methodologies to use primary, secondary, and tertiary aliphatic nitro compounds as electrophiles. The nitro group of these compounds undergoes substitution by various carbon and heteroatom nucleophiles under relatively mild conditions. 1. Introduction 2. Nucleophilic Substitution reaction of Allylic Nitro Compounds 2.1. Preparation of Allylic Nitro Compounds 2.2. Palladium-Catalyzed Substitution Reaction 2.3. Substitution Reaction Without Catalyst 3. Lewis Acid Catalyzed Substitution Reaction 3.1. Tertiary, Benzylic and Allylic Nitro Compounds 3.2. α-β -Nitro Sulfides 4. Intramolecular Nucleophilic Substitution Reaction 4.1. Cyclopropanation 4.2. Heterocycle Formation 5. Miscellaneous Substitution 6. Conclusions