Aromatic Compounds with Three Fused Carbocyclic Ring Systems: Anthracene, Phenanthrene, and Related Compounds

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Derivatives of the two hydrocarbons, anthracene and phenanthrene, C14H10, both containing three condensed benzene rings, are widely distributed in nature, for example, anthraquinone which is found, together with other polycyclic hydrocarbons, in automobile exhaust and thus, it is a minor constituent in the atmospheres of large cities. Anthracene was of commercial value as the primary intermediate for the manufacture of anthraquinone and the extensive range of polycyclic quinone dyestuffs, but anthraquinone is now largely prepared directly from phthalic anhydride and benzene. Industrial applications for phenanthrene are very few. This chapter discusses the methods of formation, synthesis, properties and reactions of anthracenes and its homologs such as alkyl-, aryl-anthracenes, aminoanthracenes, hydroxyanthracenes (anthrols), anthracenecarboxylic acids and their functional derivatives. Of the theoretically possible anthraquinones (anthracenequinones) only the 1,2-, 1,4- and 9,10-isomers are known but hydroxylated derivatives of others exist. A series of hydrocarbons known as bianthryls and their derivatives, are derived from the linkage of two anthryl units. The homologs of phenanthrene include the alkyl-phenanthrenes, aminophenanthrenes or phenanthrylamines, hydroxyphenanthrenes or phenanthrols, formyl- and acyl-phenanthrenes, phenanthrenecarboxylic acids, phenanthrene quinones and biphenanthryls.

Original languageEnglish
Title of host publicationRodd's Chemistry of Carbon Compounds
Subtitle of host publicationA Modern Comprehensive Treatise
Number of pages136
Publication statusPublished - 1964


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