Nitroalkanes. Roberto Ballini

      

      Table of Contents

      1  Cover

      2  Title Page

      3  Copyright

      4  Dedication

      5  About the Authors

      6  Acknowledgments

      7  Introduction Reference

      8  List of Abbreviations

      9  1 Synthesis of Nitroalkanes 1.1 Synthesis of Nitroalkanes 1.2 Nitration of Mesylates and Tosylates 1.3 Oxidation of Nitrogen Derivatives 1.4 Reduction of Conjugate Nitroalkenes 1.5 Nitration of Alkanes 1.6 Metal-Catalyzed Alkylation or Arylation of Nitroalkanes References

      10  2 Reduction of the Nitro Group into Amines 2.1 Representative Synthetic Applications of Nitroalkane Reductions References

      11  3 Nitro Group to Carbonyl (Nef Reaction) 3.1 Nef Reaction under Oxidative Conditions 3.2 Nef Reaction Under Reductive Conditions 3.3 Nef Reaction Under Basic Conditions 3.4 Other Methods for the Nef Reaction 3.5 Synthetic Applications of the Nef Reaction (Representative Examples) References

      12  4 Nitroaldol (Henry) Reaction 4.1 General Catalysts and Promoters 4.2 Nitroaldol Condensation 4.3 Asymmetric Henry Reaction 4.4 Aza-Henry Reaction References

      13  5 Conjugate Addition of Nitroalkanes to Electron-Poor Alkenes (Michael Reaction) 5.1 General Homogeneous Procedures 5.2 Heterogeneous Procedures 5.3 Michael Reaction under Green Solvents 5.4 Asymmetric Michael Reaction 5.5 Synthetic Applications of Michael Reaction References

      14  6 Formation of C—C Bond by Coupling Nitroalkanes with Aryl Halides 6.1 Main Procedures for Coupling Nitroalkanes with Aryl Halides 6.2 Application of C—C Coupling Nitroalkanes with Aryl Halides 6.3 Others References

      15  7 Synthesis and Reactivity of 1,3-Dinitroalkanes 7.1 Synthesis of 1,3-Dinitroalkanes 7.2 Synthetic Applications of 1,3-Dinitroalkanes References

      16  8 Formation of Carbon=Carbon Double Bonds via Nitrous Acid Elimination (NAE) 8.1 Synthesis of α,β-Unsaturated Carbonyl Derivatives 8.2 Nitroaldol Reaction, Nitrous Acid Elimination vs Water Elimination 8.3 Synthesis of Cyclic Compounds 8.4 Synthesis of Polyenes References

      17  9 α-Nitrocycloalkanones, Synthesis, and Reactivity 9.1 Synthesis of Cyclic α-Nitro Ketones 9.2 Ring Cleavage of Cyclic α-Nitro Ketones 9.3 α-Nitrocycloalkanones and Michael Reaction 9.4 α-Nitrocycloalkanones and Henry Reaction 9.5 “Zip Reaction” 9.6 Arylation of Nitrocycloalkanones References

      18  10 Acyclic α-Nitro Ketones: Synthesis and Reactivity 10.1 Synthesis of α-Nitro Ketones 10.2 Reactivity of Acyclic α-Nitro Ketones 10.3 Other