Reactions nonbenzenoid aromatic compounds

This procedure illustrates formylation by N,N-dimethylamino-methoxymethylium methyl sulfate, a compound which can be produced readily by reaction of easily available materials. 6-(Dimethylamino)fulvene is a useful intermediate for the synthesis of various f used-ring nonbenzenoid aromatic compounds. 

Bis-Wittig reaction. Synthesis of nonbenzenoid aromatic compounds by the bis-Wittig reaction has been reviewed. ... 

Oxidation Reaction. An efficient and regioselective method for iodination of electron-rich aromatic compounds has been reported by using NCS and sodium iodide in AcOH. This method is also applicable to nonbenzenoid aromatic or heteroaromatic compounds. NCS reacts with Nal to form the key intermediate ICl (eq 50). ... 

As shown in Scheme 7.14, these metal compounds act as catalysts because these cyclometalation products are highly reactive and react easily with other reagents. The substrates of these reactions are not only aromatic compounds, such as methyl phenyl ketone (Eq. (7.50)) [100,101,103] and phenylimine (Eq. (7.51)) [100,103], but also nonbenzenoid compounds, such as thiophenyl methyl ketone (Eq. (7.52)) [100,101] and cyclohexenyl methyl ketone (Eq. (7.53)) [103]. 

Pd(II)-catalyzed coupling of olefins and aromatic compounds occurs between a wide variety of olefins and aromatics not only benzenoid but also nonbenzenoid. The reaction has the following features, (i) With unsymmetrical olefins the aryl group is generally introduced to the carbon atom of the double bond, which bears fewer substituents because of steric hindrance, (ii) Electron-withdrawing groups on olefinic carbon atoms increase the yield. The examples are shown in Scheme... 

Aromatic Property that makes it possible for benzene to undergo electrophilic substitution reactions and is responsible for its stability. Other compounds with the structure of benzene are said to be aromatic, while nonbenzenoid compounds also undergo electrophilic substitution and are termed aromatic on the basis of this criterion alone. 

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