Abstract
1-Naphthyl magnesium bromide reacts with 2, 3-dichloro-1,4-naphthoquinone (I) to yield the diol (II). This is reduced to dinaphthyldichloronaphthalene (III) in boiling acetic acid with hydriodic acid. Cyclization in a sodium chloride—aluminium chloride melt gives dichloroterrylene (IV). The chlorine atoms can be removed by hydrogenation with hydriodic acid and red phosphorus under pressure, which leads to the picene derivative (V). Lower hydrogenated derivatives and some terrylene are formed in the same reduction. The dehydrogenation of (V) to terrylene (VI) is carried out with palladium—charcoal.1
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References
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© 1964 Springer-Verlag Berlin Heidelberg
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Clar, E. (1964). Hydrocarbons derived from Terrylene. In: Polycyclic Hydrocarbons. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-01668-8_7
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DOI: https://doi.org/10.1007/978-3-662-01668-8_7
Publisher Name: Springer, Berlin, Heidelberg
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