Amides and Imides

Besides the technical method starting from naphthalene, phthalic acid and its substituted derivatives can be prepared by oxidation of o-xylene to phthalic acid with potassium permanganate. This compound can be subsequently transformed via an anhydride, imide, and amide to a derivative of phthalonitrile, which is the more convenient starting material for several coordination compounds. The synthesis of the ferf-butyl-substituted dicarbonitrile, which is a very common starting material for highly soluble phthalocyanines, is shown below.97,105... 

Heterocyclic derivatives, 23 508 Heterocyclic disperse dyes, 9 419—420 Heterocyclic glycidyl imides and amides, 10 375... 

We will also include the recently determined structures of imides and amides of other alkali metals (viz. Na, K, Rb, and Cs). Only a few structures of derivatives of the heavier alkali metals are known (3), but this area can be expected to develop rapidly. 

This chiral column has been shown successfully to resolve enantiomeric mixtures (or racemates) of aromatic alcohols including l,l -bi-2-naphthol and its analogues (p. 836), aromatic hydroxy (or alkoxy) carboxylic esters and amides, amino acid derivatives, sulphoxides, cyclic imides and amides, lactones, etc. Even this list should not be regarded as limiting. The potential of this method, coupled with the simplicity of operation will undoubtedly be extensively developed and explored in the coming years. 

Hydrozirconation of imines.1 Reaction of Schiff bases containing an a-hydrogen with 1 followed by acylation provides a route to enamides and/or imides and amides. Examples ... 

Y. Kojima, Y. Kawai, IR characterization of lithium imide and amide , J. Alloys Compd. 395... 

The nucleophilicity and basicity of an amine nitrogen is vitiated by incorporation into an imide or amide linkage. The imides and amides are easily prepared by reaction of the amine with the appropriate add chloride or anhydride in the presence of a base. Amides are generally stable towards acid and base and require brutal conditions to hydrolyse them, but the small group used to protect amines was selected for their high susceptibility to nucleophilic attack. 

Fig. 69 Changes of the normalized peak area of the bands at 725 cm 1 [( ) the out-of-plane bending of the imide ring], at 3060 cm 1 [( ) C H stretching vibrations of the aromatic ring], at 1750 cm [( ) imide and amide C=0 stretching vibration], and at 2220 cm" [( ) -C=N stretching vibration]. The experiment was performed at 812 K us-ing a total flow of 50 mLx min of compressed air. Applied Spectroscopy by T. Lippert [Ref. 281], COPYRIGHT (2001) by SOC FOR APPLIED SPECTROSCOPY. Reproduced with permission of SOC FOR APPLIED SPECTROSCOPY in the format Textbook via Copyright Clearance Center...

The imides and amides of the group 1 and 2 elements clearly offer some huge advantages among chemical hydride systems most significantly the possibilities of reversible, high gravimetric and volumetric capacity solid-... 

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