Síntese de compostos α-organiltio carbonílicos utilizando sais de bunte como fonte de enxofre

Abstract

In this work, a series of α-organylthio carbonyl compounds were synthesizes from β-ketoesteres and Bunte salts, using NaOH as a reaction promoter in toluene at 100 ºC. The selectivity for the formation of two products, α-organylthio ketones and α-organylthio esters, is highlighted, based on the amount of base used. It was observed that when using 2 equivalents of base the formation of α-organylthio ketones is favored and when used 4 equivalents of base products α-organylthio esters are formed preferentially. Thus, it was possible to synthesize sixteen α-organylthio esters with yelds of 20 to 90% and six examples of α-organylthio ketones with yelds of 45 to 84%. Finally, the tolerance of reactions to a variety of groups with electron donating and withdrawing characteristics such as methoxy, methyl, trifluoromethane, nitro and chloro in ortho, meta and para positions is highlighted.