Published TCIMAIL newest issue No.196
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Wittig Olefination Reaction
The Wittig olefination, or the Wittig reaction, is a classical way to install an olefin group from a parent aldehyde, or in some cases a ketone or other less reactive carbonyl group. The Wittig olefination is incurred using a phosphonium ylide (1), which can exist as a stable compound, or can be generated from a salt form (2) in situ by treatment with base. Wittig reactions often provide the Z-olefin as the exclusive product, but varied conditions can provide the E-olefin product. Because nearly all Wittig reagents are derived from PPh3, custom or specific phosphonium ylides can be readily synthesized.
- Reagents:
- Phosphonium ylides, Phosphonium salts
- Reactants:
- Aldehydes, ketones
- Products:
- Olefins (Z- or E-)
- Scheme:
- Original literature:
-
- Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien (I. Mitteil.
- Über Triphenyl-phosphinmethylene als olefinbildende Reagenzien (II. Mitteil.1))
- Review literature:
-
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions.
Stereochemistry, mechanism, and selected synthetic aspects
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions.