Study On Synthesis And Properties Of α-Oxoketene Dithioacetals

α-ketene carbonyl compounds with a variety of different structures alkylthio groups,under acidic conditions, these different structures alkylthio groups will be separted fromα-ketene carbonyl compounds and becomed different thiols. ketene carbonyl compoundsoccur as a thiol equivalent in organic reactions. in this article, ketene carbonyl compoundsrealized the reaction that they acted as the alternative thiol reagents. In this experiment,twelve different structures of ketene carbonyl compounds were synthesized, mainlyincludes four alkylthio: ethyl group, butyl group, benzyl group, p-tert-butylbenzyl group.α-ketene carbonyl compounds having tert-butyl benzyl group was the core of the researchand three three new ketene carbonyl compounds who have tert-butyl benzyl group weresynthesized, namely3-(bis(4-tert-butylbenzylthio)methylene)pentane-2,4-dione,2-(bis (4-tert-butylbenzylthio)methylene)-3-oxo-N-phenylbutanamide, ethyl-2-(bis(4-tert-butylbenzylthio)methylene)-3-oxobutanoate. The three compounds were used in the Michael Additionreaction and mercaptal reaction, ten kinds of unsaturated carbonyl compounds and fourkinds of double-sided unsaturated carbonyl compounds were be synthesized by AldolReaction. ketene carbonyl compounds can occur the Michael addition with with one-sidedα,β-unsaturated carbonyl compounds, but it is hard to react with double-sidedα,β-unsaturated carbonyl compounds. In Thioacetalization reaction, ketene carbonylcompounds react with benzaldehydes, as occur the reaction of the thiol compound, and onekind of sulfide compound was synthesized. By observing the result of Michael additionreaction and the Thioacetalization reaction about these three ketene carbonyl compoundswith tert-butyl benzyl group structure to dectect the reactivity, mainly nucleophilic properties.Compare the strength of nucleophilic properties between them in the reaction, exprole theaffect about the structural differences to nucleophilic properties. While exploring differentreaction conditions on the reaction, to explore an effective environmental pollution syntheticroute, better to put carbonyl ketene applied to the thiol reagent to substitute for thegeneration of thiol reagents provide some theoretical basis for research and development.