Wittig reaction

Not to be confused with Wittig rearrangement.

Wittig reaction
Named after Georg Wittig
Reaction type Coupling reaction
Reaction
aldehyde or ketone
+
triphenyl phosphonium ylide
↓
alkene
+
(Ph)3P=O
Conditions
Typical solvents typically THF or diethyl ether
Identifiers
March's Advanced Organic Chemistry 16–44 (6th ed.)
Organic Chemistry Portal wittig-reaction
RSC ontology ID RXNO:0000015 checkY
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The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes.[1][2][3] Most often, the Wittig reaction is used to introduce a methylene group using methylenetriphenylphosphorane (Ph3P=CH2). Using this reagent, even a sterically hindered ketone such as camphor can be converted to its methylene derivative.

Wittig Reaction
  1. ^ Maercker, A. Org. React. 1965, 14, 270–490.
  2. ^ W. Carruthers, Some Modern Methods of Organic Synthesis, Cambridge University Press, Cambridge, UK, 1971, 81–90. (ISBN 0-521-31117-9)
  3. ^ R. W. Hoffmann (2001). "Wittig and His Accomplishments: Still Relevant Beyond His 100th Birthday". Angewandte Chemie International Edition. 40 (8): 1411–1416. doi:10.1002/1521-3773(20010417)40:8<1411::AID-ANIE1411>3.0.CO;2-U. PMID 11317288.