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DOI: 10.1055/s-1997-5754
Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones
Publication History
Publication Date:
31 December 2000 (online)
4-(p-Chlorophenyl)-3-hydroxythiazole-2(3H)-thione (3) can be prepared in good yields and in useful quantities from p-chloro acetophenone (1). 0-Alkylation of the cyclic thiohydroxamic acid 3 via the respective potassium or the tetraethyl ammonium salts affords the esters 4. A slightly modified procedure allows the conversion of the acid 3 to the mixed anhydrides 5. The esters 4 and the anhydrides 5 are colorless to yellowish crystalline compounds which show a good shelf life. Visible light photolysis of the N-alkoxy derivatives 4e-g and reactive hydrogen donors affords substituted tetrahydrofurans 7 or tetrahydropyrans 8 via an alkoxyl radical pathway.
thiazolthiones - thiohydroxamic acid - alkoxyl radical precursor - O-alkylation