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Synthesis 1988; 1988(11): 833-847
DOI: 10.1055/s-1988-27726
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Functionalized Nitroalkanes as Useful Reagents for Alkyl Anion Synthons

Goffredo Rosini* , Roberto Ballini
  • *Dipartimento di Chimica Organica dell' Università, Viale Risorgimento n. 4, I-40136 Bologna, Italy
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Publication Date:
20 August 2002 (online)

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This article reviews new methodologies to use aliphatic nitro compounds in assembling carbon atoms and functional groups without the problems associated with the utilization of organometallic species. The reductive, direct or indirect denitration reaction is the key step of the procedures, in which primary nitroalkanes are used as convenient reagents for alkyl anion synthons. 1. Introduction 2. General Reactivity of Nitroalkanes 3. Reductive Denitration Reactions 4. Denitration of 2-Nitro-Ketone Tosylhydrazones 5. New Methodologies to Prepare Functionalized Nitroalkanes by Chain-Lengthening Reactions 6. Utilization of Functionalized Nitroalkanes in Synthesis 6.1. Synthesis of Ketones, Aldehydes, Esters, Nitriles, Sulfoxides and Sulfones 6.2. 4-Nitro-2-butanone Ethylene Acetal as d3-Reagent for the 3-Oxobutyl Anion Synthon 6..3. 3-Nitropropanal Ethylene Acetal as a d3-Reagent for the 3-Oxopropyl Anion Synthon 6.4. Methyl 8-Nitrooctanoate as a d8-Reagent for the 7-Methoxy-carbonylheptyl Anion Synthon 6.5. Utilization of (Z)-1-Nitro-3-alkenes in Synthesis 6.6. Synthesis of α-Methylene Carbonyl Compounds 6.7. Synthesis of 1,5-Dicarbonyl Compounds 6.8. Selective Alkenylation and Hydroxyalkylation of Cycloketones 6.9. Synthesis of Macrocyclic Lactones and Ketones 7. Additional Synthetic Applications of Direct Denitration 8. Selective α-Deuteration of Ketones 9. Conclusions

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