Selective preparation of polycyclic aromatic hydrocarbons. Part 5.1 Bromination of 2, 7-di-tert-butylpyrene and conversion into pyrenoquinones and their …

T Yamato, M Fujimoto, A Miyazawa…

Index: Yamato, Takehiko; Fujimoto, Masakazu; Miyazawa, Akira; Matsuo, Koji Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 8 p. 1201 - 1207

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Abstract

The bromination of 2, 7-di-tert-butylpyrene 1 with 1.1 mol equiv. and 2.2 mol equiv. of bromine in a carbon tetrachloride solution afforded 1-bromo-2, 7-di-tert-butylpyrene 2a and a mixture of 1, 6-dibromo-(3a) and 1, 8-dibromo-2, 7-di-tert-butylpyrene (3b) in 85 and 73% yield, respectively. On the other hand, when the same reaction was carried out with 6.0 mol equiv. of bromine in the presence of iron powder, an acid-catalysed rearrangement of ...

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