Abstract
Publisher Summary This chapter discusses the formation of benzene derivatives by cyclization reactions. Diels-Alder reactions using dimethyl acetylenedicarboxylate as the dienophile allow the formation of benzene derivatives after an oxidation step and removal of the methoxycarbonyl groups. Several important general features of the electrophilic addition-with-elimination reactions of electrophiles with arenes are discussed. These include protonation reactions; metallation reactions; group IV electrophiles undergoing alkylation reactions, chloromethylation reactions, acylation reactions, and formylation reactions; group V electrophiles undergoing nitration reactions, nitrosation reactions, and azo-coupling reactions; group VI electrophiles undergoing hydroxylation reactions; sulfur electrophiles; group VII electrophiles undergoing fluorination, chlorination and bromination, and iodination reactions. Additions to arenes are characterized by the reduction of arenes and functional groups, thermal cycloaddition reactions, and photocycloaddition reactions. In a pair of benzene-Dewar benzene isomers it is possible to arrange the substituents such that the thermodynamic relationships of the two isomers help to stabilize the non-aromatic structure. A number of aromatization reactions are also presented that utilizes alkali metal derivatives of ethylenediamine.
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