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Issue 12, 2002
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Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

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Abstract

A temperature-sensitive photochemical nucleophilic aromatic substitution on 4-nitroanisole by a hydroxide ion in homogeneous solutions, in a two-phase system under phase-transfer catalysis conditions, and in the microwave field is reported. It was found that reaction regioselectivity dramatically changes with temperature in the region of −20 to 196 °C. The quantum yield of the 4-methoxyphenol formation was found to be temperature independent, in contrast to that of the 4-nitrophenol formation, suggesting that there is a temperature dependent process occurring after the partitioning between replacement of the nitro group and the methoxy group has taken place. The reaction was also investigated by using quantum chemical calculations. A technique for microwave-assisted photochemical synthesis is proposed as an efficient and practical tool for organic synthesis.

Graphical abstract: Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

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Article information


Submitted
18 Sep 2002
Accepted
18 Oct 2002
First published
13 Nov 2002

Photochem. Photobiol. Sci., 2002,1, 1012-1016
Article type
Paper

Temperature-sensitive photochemical aromatic substitution on 4-nitroanisole

P. Klán, R. Růžička, D. Heger, J. Literák, P. Kulhánek and A. Loupy, Photochem. Photobiol. Sci., 2002, 1, 1012
DOI: 10.1039/B209010D

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