Nitro chemistry

In the organic nitro chemistry era of the 11 flies and early sixties, a great emphasis of the research was directed toward the synthesis of new compounds that would be useful as potential ingredients in explosives and propellants. 

It is the purpose of the series to review the field of organic nitro chemistry in its broadest sense by including structurally related classes of compounds such as nitroamines, nitrates, nitrones, and nitrile oxides. It is intended that the contributors, who are active investigators in various facets of the field, will provide a concise presentation of recent advances that have generated a renaissance in nitro chemistry research. 

In recent years, the importance of aliphatic nitro compounds has greatly increased, due to the discovery of new selective transformations. These topics are discussed in the following chapters Stereoselective Henry reaction (chapter 3.3), Asymmetric Micheal additions (chapter 4.4), use of nitroalkenes as heterodienes in tandem [4+2]/[3+2] cycloadditions (chapter 8) and radical denitration (chapter 7.2). These reactions discovered in recent years constitute important tools in organic synthesis. They are discussed in more detail than the conventional reactions such as the Nef reaction, reduction to amines, synthesis of nitro sugars, alkylation and acylation (chapter 5). Concerning aromatic nitro chemistry, the preparation of substituted aromatic compounds via the SNAr reaction and nucleophilic aromatic substitution of hydrogen (VNS) are discussed (chapter 9). Preparation of heterocycles such as indoles, are covered (chapter 10). 

J. H. Boyer, Organic Nitro Chemistry Series 1 Nitroazoles. The C-Nitro Derivatives of Five Membered N- and N,0-Heterocycles, p. 147. VCH Publishers, Deerfield Beach, FL, 1986. 

The beginning of aliphatic nitro chemistry goes back to 1872 when V. Meyer and O. Stueber achieved the synthesis of 1-nitropentane by reacting 1-iodopentane with silver nitrite. This report led to an impetus of research in the field, resulting in numerous publications. 

Another important development in the field was the discovery of the vapor-phase nitration in the 1930s by H. Hass and his students at Purdue University. It led in 1940 to the commercial production of lower molecular weight nitroalkanes [Cl to C4] at a pilot plant of the Commercial Solvents Corporation in Peoria, Illinois. In the organic nitro chemistry era of the fifties and early sixties, a great emphasis of the research was directed towards the synthesis of new compounds that would be useful as potential ingredients in explosives and propellants. 

N. Ono, The Nitro Group in Organic Synthesis., Organic Nitro Chemistry Series., Wiley-VCH, Weinheim, Chapter 2, 3-29 (2001). 

H. O. Larson, in The Chemistry of the Nitro and Nitroso Groups, Part 1, Organic Nitro Chemistry Series, Ed. H. Eeuer., Wiley-Interscience, Weinheim, Chapter 6, 301-348 (1969). 

Box, J. Chem. Soc. Perkin Trans. 1., 1999,749 (c) J. P. Adams and J. R. Paterson, J. Chem. Soc. Perkin Trans. 1., 2000, 3695 (d) J. H. Boyer, in The Chemistry of the Nitro andNitroso Groups, Part 1, Organic Nitro Chemistry Series, Ed. H. Fener, Wiley-Interscience, Weinheim, 229 (1969) (e) H. O. Larson, in The Chemistry of the Nitro andNitroso Groups, Part 1, Organic Nitro Chemistry Series, Ed. H. Fener., WUey-Interscience, Weinheim, Chapter 6, 301-348 (1969). 

J. W. Fischer, in Nitro Compounds Recent Advances in Synthesis and Chemistry, Organic Nitro Chemistry Series, Eds. H. Feuer and A. T. Neilsen, Wiley-VCH, Weinheim 315-325 (1990). 

K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis , in Organic Nitro Chemistry, H. Feuer, ed., VCH Publishers, Inc., New York, 1988. 

G.A. Olah, R. Malhotra u. S. C. Narang, Organic Nitro Chemistry Series in H. Feuer. Nitration, Methods... 

N. Ono in H. Feuer u. A. T. Nielsen Organic Nitro Chemistry Series Nitro Compounds, S. 1-135, The... 

Organic Nitro Chemistry Series, Verlag Chemie, Weinheim 1989, Chapter 1, ref. 2 to 6. 

---