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Chemistry · Glossary

What is Phosphonium ylides?

Also known as: phosphonium salt · phosphonium ylide · stabilised ylide

Definition 27.1 University Chemistry — Year 2 · Chapter 27 — Wittig and Other C=C Forming Reactions

A phosphonium salt R3P+−CH2R′ X−\mathrm{R_3P^+{-}CH_2R'\ X^-} is made by bimolecular substitution of a halogenoalkane by a phosphine, usually triphenylphosphine PhX3P\ce{Ph3P}. Removing a hydrogen from the carbon bound to phosphorus gives a phosphonium ylide, a neutral molecule with adjacent opposite charges, Ph3P+−CH−−R′\mathrm{Ph_3P^+{-}CH^-{-}R'}, also written Ph3P=CHR′\mathrm{Ph_3P{=}CHR'}. A stabilised ylide carries on that carbon an electron-withdrawing group (an ester, a ketone, a nitrile) that delocalises the negative charge.

Methylidenetriphenylphosphorane, the simplest ylide. Triphenylphosphine displaces iodide from iodomethane; butyllithium removes a proton from the methyl group. The two structures on the right are two ways of writing the same molecule: the charge-separated one is the closer to reality.
Methylidenetriphenylphosphorane, the simplest ylide. Triphenylphosphine displaces iodide from iodomethane; butyllithium removes a proton from the methyl group. The two structures on the right are two ways of writing the same molecule: the charge-separated one is the closer to reality.
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