Nitro compounds alicyclic

If iV,iV-dimethylethylenediamine is used as the base, allylic nitro compounds are obtained n good yields from both acyclic and alicyclic ketones fEqs. 3.22 and 3.23. "... 

Aliphatic and alicyclic ketones condense with primary nitroalkanes under the influence of A,A-dimethylethylenediamine to yield ally lie nitro compounds as mixtures of geometrical isomers, e.g. equation 125408. 

N. Kornblum, The Synthesis of Aliphatic and Alicyclic Nitro Compounds, Org. React.,... 

Kornblum, N. The synthesis of aliphatic and alicyclic nitro compounds. In Cope, A. C., Ed.-in-Chief "Organic Reactions", Vol. 2 John Wiley Sons, Inc. New York, 1962 pp. 101-156. 

The aminolysis of the aryl 5-methyl thiocarbonates (62-64) by secondary alicyclic amines in aqueous solution at 25 °C proceeded by a stepwise mechanism in the case of the 4-nitro compound (62), but by a concerted mechanism for the other two substrates (63, 64).52... 

Nitro compounds were the objective of much research. Certain aspects of this field of organic chemistry are discussed in many monographs and reviews. Well known treatise is a monograph on the chemistry of nitro and nitroso groups edited by Feuer [1], The chemistry and technology of aromatic nitro compounds is considered in monographs [2-4], Much attention has been given to unsaturated [5], aliphatic and alicyclic nitro compounds [6],... 

Novikov SS, Shveihgeimer GA, Sevastyanova BB et al (1974) Chemistry of aliphatic and alicyclic nitro compounds. Chemistry, Moscow... 

Komblum, N. 1962. The synthesis of ahphatic and alicyclic nitro compounds. Organic Reactions, 12 101-56. 

Olefin synthesh. Komblum ei a . have described a new synthesis of tetrasubsti-tuted olefins from vicinal dinitro compounds. There are several methods for conversion of aliphatic and alicyclic nitro compounds into nic-dinitro compounds, the most useful of which is a procedure of Seigle and Hass. A nitroparafhn is converted into (he lithium salt (I) by treatment with lithium methoxidc and this is then treated with bromine to form a bromonilro compound (2). Reaction of (2) with a second equivalent of the nitro-R.. NO,, ... 

Reactions of the replacement by hydrogen of the tertiary nitro group in aliphatic and alicyclic compounds were recently described by Kornblum and co-workers (145). They occur at room temperature when the nitro compounds are treated with the sodium salt of methyl mercaptan. 

Alif atic and alicyclic nitro compounds Photoconductivity of nitro compounds Photolysis References... 

Kornblum, N. The synthesis of aliphatic and alicyclic nitro compounds. Org. React. 1962,12, 101-156. 

Metal hydrides such as lithium tetrahydridoaluminate have been used for reduction of aliphatic and alicyclic nitro to amino compounds in general, 2 moles of this aluminate are applied per mole of nitro compound. However, aromatic nitro compounds are usually reduced thereby only to the azo stage. Indeed, apart from special cases, the reduction of nitro compounds by lithium tetrahydridoaluminate has only slight practical importance.27 Sodium tetra-hydridoborate had been recommended for reduction of o-nitrophenol in the presence of a palladium-charcoal catalyst.73... 

S. S. NOVIKOV. G. A. SHVEKHGEIMER, V. V. SEVOSTYANOVA and V. A. SHLAPOCHNIKOV, Chemistry of Aliphatic and Alicyclic Nitro Compounds (in Russian), Chapter X, Khimiya, Moscow (1974). 

Protonated aliphatic/alicyclic nitro compounds have not been studied to the same extent as the nitroarenes. However, the isomeric [C2H6N02]+ ions and their rearrangement in the gas phase have been subject to studies . The protonated ethyl nitrite and nitroethane were generated by proton transfer from different Br0nsted acids. In addition, protonated ethyl nitrite was obtained as a result of addition of NO+ to ethanol. The existence of two different [C2H6N02]" structures, i.e. protonated ethyl nitrite and protonated nitroethane, was demonstrated. Slow isomerization of protonated nitroethane to protonated ethyl nitrite has been elucidated see Scheme 40. 

Prim, and sec. amines from oximes Reductive rearrangement s. 72, 411 Cyclic imines from alicyclic nitro compounds... 

The radical anions of acyclic and alicyclic nitro compounds have been investigated in aqueous media. They have been obtained for primary, secondary, and tertiary nitro derivatives ... 

Alicyclic hydroxamic acids undergo several specific oxidative cleavage reactions which may be of diagnostic or preparative value. In the pyrrolidine series compounds of type 66 have been oxidized with sodium hypobromite or with periodates to give y-nitroso acids (113). Ozonolysis gives the corresponding y-nitro acids. The related cyclic aldonitrone.s are also oxidized by periodate to nitroso acids, presumably via the hydroxamic acids.This periodate fission was used in the complex degradation of J -nitrones derived from aconitine. 

This chapter is an extension of Chapter 1 and discusses the more recent research into energetic compounds which contain strained or caged alicyclic skeletons in conjunction with C-nitro functionality. This chapter complements Chapter 1 by providing case studies which show how the same methods and principles that introduce C-nitro functionality into simple aliphatic compounds can be used as part of complex synthetic routes towards caged polynitrocycloalkanes. The chemistry used for the synthesis of caged structures can be complex but the introduction of C-nitro functionality follows the same principles as discussed in Chapter 1. It is suggested that chemists who are not familiar with this field of chemistry consult Chapter 1 before reading this chapter. 

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