Amides and Related Compounds

Representative examples of structurally characterized self-assembled alkali metal amides and related compounds are listed in Table 6.2. 

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It was further shown that such equations could be extended to a wide variety of amides and related compounds and even allowed the prediction of the degradation products of agrochemicals of the benzoylphenylurea type [13]... 

Phosphoms halides are subject to reactions with active hydrogen compounds and result in the elimination of hydrogen halide. They are convenient reagents in the synthesis of many esters, amides, and related compounds. However, because the involved hydrogen halide frequendy catalyzes side reactions, it is usually necessary to employ a hydrogen halide scavenger to remove the by-product. 

Trimethylsilyl cyanide. This reagent readily silylates alcohols, phenols, and carboxylic acids, and more slowly, thiols and amines. Amides and related compounds do not react with this reagent. The reagent has the advantage that a volatile gas (HCN is highly toxic) is the only byproduct. 

Resonance Energies of Aliphatic Acids, Esters, Amides, and Related Compounds... 

Organomagnesium amides and related compounds with group 15-bonded ligands 106... 

Challis, B. and Challis, J. (1979). Amides and related compounds. In Comprehensive Organic Chemistry, Nitrogen Compounds, Carboxylic Acids, Phosphorous Compounds, Sutherland, I.O. (ed.), Vol. 2, p. 957. Pergamon Press, Oxford... 

REACTIONS OF DIHALOCARBENES WITH AMINES, IMINES, AMIDES AND RELATED COMPOUNDS... 

A number of reagents derived from nitrate salts and acid anhydrides have been reported for the V-nitration of amides and related compounds. Crivello first reported the use of metal nitrates in trifluoroacetic anhydride (TFAA) for the nitration of aromatic systems. Chapman... 

The instability of primary nitramines in acidic solution means that the nitration of the parent amine with nitric acid or its mixtures is not a feasible route to these compounds. The hydrolysis of secondary nitramides is probably the single most important route to primary nitramines. Accordingly, primary nitramines are often prepared by an indirect four step route (1) acylation of a primary amine to an amide, (2) A-nitration to a secondary nitramide, (3) hydrolysis or ammonolysis with aqueous base and (4) subsequent acidification to release the free nitramine (Equation 5.17). Substrates used in these reactions include sulfonamides, carbamates (urethanes), ureas and carboxylic acid amides like acetamides and formamides etc. The nitration of amides and related compounds has been discussed in Section 5.5. 

Dinihogen pentoxide in aprotic solvents is not usually used for nitrolysis reactions. The nitrogen atoms of amides and related compounds are usually quite electron deficient and these reagents are too mild to affect cleavage. However, the nittolysis of symmetrical... 

Amides and related compounds have been thoroughly investigated as ligands for alkali metals. Studies in solution have been made using various physicochemical techniques these, and MO calculations, show that the interaction of amides with M+ is via the carbonyl function.56,57 This leads to a delocalization of the amide N electron pair and so it is possible to follow the decrease in C—O, and the increase in C—N, bond orders using IR spectroscopy. X-Ray crystal structures of amide complexes have shown both types of complexation interaction to be present (Table 2). 

An excellent account of the role of metal ions in the solvolysis of amides and related compounds. 

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