Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones

Jens Hartung; Michaela Schwarz

doi:10.1055/s-1997-5754

Synlett 1997; 1997(7): 848-850
DOI: 10.1055/s-1997-5754

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Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones

Jens Hartung^* , Michaela Schwarz

^*Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Telefax: (internat.) +49 (0)931/888 4606, E-mail: hartung@chemie.uni-wuerzburg.de

Abstract

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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

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