Abstract
Stable crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylates, and strong NH-acids, such as acetanilide, 4-methylacetanilide, 2-cyanoacetanilide, 4-bromoacetanilide, 4-methoxyacetanilide, succinimide, malimide, or phthalimide. These stabilized phosphoranes exist as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.
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