Reactions of copper(II) halides with aromatic compounds—IX

Add time:08/01/2019    Source:sciencedirect.com

2-Alkoxynaphthalenes undergo halogenation with copper(II) halides in the 1-position though 2-benzyloxynaphthalene with copper(II) bromide gives additionally di-β-naphthol, 1-benzyl-2-naphthol, and benzyl bromide. The reaction of 1-alkoxynaphthalenes with copper(II) halides leads to 1-alkoxy-4-halogenonaphthalenes and 4,4′-dialkoxy-1,1′-binaphthyls. 8-Chloro-1-methoxynaphthalene is afurther product from the reaction of 1-methoxynaphthalene and copper(II) chloride. The reactions are postulated to proceed via the radical cation of the alkoxynaphthalene formed in an electron-transfer reaction. This can then either react further with the copper(II) halide or dimerize.

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