All books

Professional

Apps About Coach Log in Start reading

Chemistry · Glossary

What is Wittig reaction?

Also known as: oxaphosphetane

Definition 27.3 University Chemistry — Year 2 · Chapter 27 — Wittig and Other C=C Forming Reactions

The Wittig reaction of a phosphonium ylide with an aldehyde or a ketone gives an alkene and triphenylphosphine oxide:

Ph3P=CHR+R′CHO⟶R′CH=CHR+Ph3P=O.\mathrm{Ph_3P{=}CHR + R'CHO \longrightarrow R'CH{=}CHR + Ph_3P{=}O}.

It goes through an oxaphosphetane, a four-membered ring of phosphorus, two carbons and oxygen, formed by the ylide carbon bonding to the carbonyl carbon while the carbonyl oxygen bonds to phosphorus.

The Wittig reaction. The ylide carbon and the carbonyl carbon bond together while oxygen bonds to phosphorus, in one step: the oxaphosphetane. Its ring then opens the other way, breaking the P-C and C-O bonds: the C=C bond forms between the two former reacting carbons, and the P=O bond of triphenylphosphine oxide forms at the same time. The Wittig reaction. The ylide carbon and the carbonyl carbon bond together while oxygen bonds to phosphorus, in one step: the oxaphosphetane. Its ring then opens the other way, breaking the P-C and C-O bonds: the C=C bond forms between the two former reacting carbons, and the P=O bond of triphenylphosphine oxide forms at the same time.
The Wittig reaction. The ylide carbon and the carbonyl carbon bond together while oxygen bonds to phosphorus, in one step: the oxaphosphetane. Its ring then opens the other way, breaking the P−C\ce{P-C} and C−O\ce{C-O} bonds: the C=C\ce{C=C} bond forms between the two former reacting carbons, and the P=O\ce{P=O} bond of triphenylphosphine oxide forms at the same time.
Read in context →