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Additional recommended knowledge
The reaction is named after two chemists who devoted part of their career to research into this synthetic method, the German chemist Kurt Lehmsted and the Romanian chemist Ioan Tănăsescu. Variations to the reaction name are the Lehmsted-Tănăsescu-reaction, Lehmsted-Tănăsescu-acridone-synthesis en Lehmsted-Tanasescu-acridone-synthesis.
In the first step of the reaction mechanism the precursor molecule 2-nitrobenzaldehyde 4 is protonated, often by sulfuric acid, to intermediate 5, followed by an electrophilic attack to benzene (other arenes can be used as well). The resulting benzhydrol 6 cyclisizes to 7 and finally to compound 8. Treatment of this intermediate with nitrous acid (sodium nitrite en sulfuric acid) leads to the N-nitroso acridone 11 via intermediates 9 en 10. The N-nitroso group is removed by an acid in the final step. The procedure is an example of a one-pot synthesis.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Lehmstedt-Tanasescu_reaction". A list of authors is available in Wikipedia.|