Abstract
Stable crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine and dialkyl acetylenedicarboxylates in the presence of 1-methylimidazole-2-thiol. These sulfur-containing phosphoranes exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group. Using dibenzoylacetylene as Michael acceptor, yields 2-[1-methyl-1 H -imidazole-2-yl)sulfanyl]-1,4-diphenyl-butane-1,4-dione.
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