Issue 4, 2000

Titanium dioxide photocatalyzed oxygenation of naphthalene and some of its derivatives

Abstract

The titanium dioxide photocatalyzed oxygenation of naphthalene in water gives (E,Z )-2-formylcinnamaldehydes and 1,4-naphthoquinone besides traces of naphthols. 1-Substituted naphthalenes (both with an electron-withdrawing and -donating group) are likewise oxidised at about the same rate with a similar product distribution. The evidence obtained supports the hypothesis that the reaction involves transfer of a hydroxy group to naphthalene and reduction of oxygen to superoxide followed by coupling of the two species. In organic solvents the reaction is slower, more selective (a cyano group inhibits the reaction) and leads to phthalic anhydride and 1,4-naphthoquinone. The relation with the solvent-dependent course of the ozonation of the same substrates is commented upon.

Article information

Article type
Paper
Submitted
10 Nov 1999
Accepted
01 Feb 2000
First published
14 Mar 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 699-704

Titanium dioxide photocatalyzed oxygenation of naphthalene and some of its derivatives

F. Soana, M. Sturini, L. Cermenati and A. Albini, J. Chem. Soc., Perkin Trans. 2, 2000, 699 DOI: 10.1039/A908945D

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