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the removal of the acidic hydrogen attached to the carbon adjacent to the phosphorus atom in a quaternary phosphonium salt, results directly in a Ylide
A neutral dipolar molecule known as a ylide or ylid has two formally positively charged heteroatoms that are physically linked, both of which have full octets of electrons.
Ylides are substances where one atom is positively charged and the other is negatively charged. They are zwitterions, which are single molecules with both positive and negative charges. There are numerous techniques to make mononuclear ylide complexes of gold(I) and gold(III).
All of the ylides displayed here are solid bases. They are susceptible to oxygen and protonation by water and alcohols, just like other strongly basic organic reagents. As demonstrated, water breaks down alkylidenephosphoranes into hydrocarbons and phosphine oxides.
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