Roberto Ballini - Nitroalkanes

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 Reactions References

19 11 Nitro Cyclopropanes: Synthesis and Applications 11.1 Synthesis of Nitro Cyclopropanes 11.2 Applications of Nitrocyclopropanes References

20 12 Nitroalkanes as Source of Dicarbonyls 12.1 1,2-Dicarbonyl Derivatives 12.2 1,3-Dicarbonyl Derivatives 12.3 1,4-Dicarbonyl Derivatives 12.4 1,5-Dicarbonyl Derivatives References

21 13 Nitroalkanes as Source of Spiroketals 13.1 1,6-Dioxaspiro[4.4]nonanes 13.2 1,6-Dioxaspiro[4.5]undecanes 13.3 1,6-Dioxaspiro[4.6]undecanes 13.4 1,7-Dioxaspiro[5.5]undecanes and 1,7-Dioxaspiro[5.6]dodecanes References

22 Index

23 End User License Agreement

1 Chapter 1 Table 1.1 NaBH 4/SiO 2reduction of nitroalkenes (select... Table 1.2 Comparative reduction of nitroalkenes with methods (i)–(iii)... Table 1.3 Reduction of nitroalkenes with NaCNBH 3(selected exampl... Table 1.4 Stereoselective reduction of nitroalkenes (selected examples) Table 1.6 Asymmetric nitromethylation of cyclic allyl esters (selected examp... Table 1.7 Two-step process of nitro alkylation of allylic alcohols (selected... Table 1.8 Two carbon homologation of vinyl bromides or triflates (selected e...

2 Chapter 2 Table 2.1 Reduction of nitroalkanes possessing heteroaromatic structures (se...Table 2.2 Reduction of nitroalkanes by H 2/Ni/Al-SBA-15 (selected ...

3 Chapter 3Table 3.1 Nef reaction by ozonolysis of nitronate (selected examples).Table 3.2 Nef reaction by CAN (selected examples).Table 3.3 Nef reaction with NaH/KMnO 4.Table 3.4 Nef reaction with KOH/KMnO 4–MgSO 4.Table 3.5 Nef reaction promoted by MCPA (selected examples).Table 3.6 Primary nitroalkanes to carboxylic acid by basic phosphate buffer ...Table 3.7 Nef reaction by TPAP/NMO/MS.Table 3.8 Nef reaction by Oxone (selected examples).Table 3.9 Nef reaction promoted by DMD (selected examples).Table 3.10 Nef reaction promoted by Cu(OAc) 2(selected examples).Table 3.11 Nef reaction with IL/SPB (representative examples).Table 3.12 Nef reaction by KMnO 4under flow process (representati...Table 3.13 Nef reaction promoted by TiCl 3–NH 4OAc...Table 3.14 Nef reaction promoted by VCl 2(representative examples).Table 3.15 Nef reaction promoted by PMe 3/additive Aor ...Table 3.16 Nef reaction by basic silica gel (representative examples).Table 3.17 Nef reaction promoted by DBU (representative examples).Table 3.18 Nef reaction promoted by NaNO 2/AcOH (representative ex...Table 3.19 Nef reaction promoted by KH/Me 3SiCl (representative ex...Table 3.20 Nef reaction promoted by SiO 2–TBD (representativ...

4 Chapter 4Table 4.1 Henry reaction promoted by Amberlyst A21 (representative examples).Table 4.2 Henry reaction promoted by SiO 2/MW (representative exam...Table 4.3 Henry reaction promoted by powered KOH (representative examples).Table 4.4 Henry reaction promoted by Mg–Al (3 : 1) hydrotalcite (repre...Table 4.5 Henry reaction promoted by ISOLUTE Si carbonate (representative exa...Table 4.6 Henry reaction promoted by PEI (representative examples).Table 4.7 Henry reaction promoted by PS-DMAP (representative examples).Table 4.8 Henry reaction promoted by K 2CO 3(representa...Table 4.9 Henry reaction promoted by guanidine ( I) (representative ex...Table 4.10 Henry reaction promoted by Et 3N/SiO 2(repre...Table 4.11 Henry reaction promoted by KI@Fe 3O 4...Table 4.12 Henry reaction promoted by NaOH/CTACl/H 2O (representat...Table 4.13 Henry reaction promoted by CTAOH (representative examples).Table 4.14 Henry reaction promoted by Ba(OH) 2(representative exa...Table 4.15 Henry reaction promoted by CTAB/phosphate buffer/H 2O, ...Table 4.16 Henry reaction in (i) TMG·F 3Ac or (ii) TMG Lac (r...Table 4.17 Henry reaction promoted by [bmim][BF 4]/DBU (representa...Table 4.18 Nitroaldol condensation promoted by basic Al 2O 3...Table 4.19 Nitroaldol condensation promoted under MW, NH 4OAc, and...Table 4.20 Nitroaldol condensation promoted under ultrasound, NH 4...Table 4.21 Nitroaldol condensation under FDU-ED catalysis (representative ex...Table 4.22 Nitroaldol condensation promoted by FeCl 3-piperidine (...Table 4.23 Henry reaction of sugars with BrCH 2NO 2unde...Table 4.24 Henry reaction promoted by CuBr, Py, MeOH, and ligand D(s...Table 4.25 Anti-selective Henry reaction by [(bisurea-salen)Co]·OBz...