Master Organic Chemistry Reaction Guide

Wittig Reaction – conversion of ketones/aldehydes to alkenes

Description: The Wittig reaction is a useful way of forming alkenes from phosphorus ylides (“Wittig Reagents”) and aldehydes or ketones.
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Further Reading

  1. Über Triphenyl‐phosphin‐methylene als olefinbildende Reagenzien (I. Mitteil.
    Georg Wittig, Ulrich Schöllkopf Ber. 1954 87 (9), 13318
    DOI: 10.1002/cber.19540870919
  2. Über Triphenyl‐phosphinmethylene als olefinbildende Reagenzien (II. Mitteil.1))
    Georg Wittig, Werner Haag Ber. 1955, 88 (11), 1654
    DOI: 10.1002/cber.19550881110
    The first two papers by Nobel Laureate Prof. Georg Wittig on a new olefination reaction based on phosphonium ylides.
  3. From Diyls to Ylides to My Idyll
    Georg Wittig. Science 1980, 210 (4470), 600
    DOI: 1126/science.210.4470.600
    Prof. Wittig’s Nobel Lecture, in which he talks about how he first discovered phosphonium ylides on accident while trying to synthesize pentavalent nitrogen compounds, as well as the origin of the term ‘ylide’.
  4. METHYLENECYCLOHEXANE
    George Wittig and U. Schoellkopf. Synth. 1960, 40, 66
    DOI: 10.15227/orgsyn.040.0066
    Reproducible and tested procedure for methylidenation with phosphonium ylides reported by Nobel Laureate Prof. G. Wittig.
  5. Unusual solvent effects in the Wittig reaction of some ketones indicating initial one-electron transfer
    George A. Olah and V. V. Krishnamurthy. Journal of the American Chemical Society 1982, 104 (14), 3987-3990
    DOI: 1021/ja00378a035
    This paper, unusually from Nobel Laureate Prof. George Olah, shows that single-electron transfer reduction can take place when reacting sterically hindered ketones (e.g. 2-adamantanone) with bulky phosphonium ylides.
  6. Reactivity and Selectivity in the Wittig Reaction: A Computational Study
    Raphaël Robiette, Jeffery Richardson, Varinder K. Aggarwal, and, and Jeremy N. Harvey. Journal of the American Chemical Society 2006 128 (7), 2394-2409
    DOI: 1021/ja056650q
    A computational investigation of the Wittig reaction that attempts to explain the stereochemistry of the products (unstabilized ylides yield Z-alkenes and stabilized ylides give E-alkenes).

Comments

Comment section

8 thoughts on “Wittig Reaction – conversion of ketones/aldehydes to alkenes

  1. Isn’t the final Alkene confirmation dependent on the R-groups of the Ylide, Cis from an unstablized ylide and trans from the semi/fully stabilized ylide?

  2. Are there Wittig reagents that are more commonly used? How do you know what reagent to use? I have a lot of problems where we’re given the final product and then have to show how they can be synthesized, but I’m really confused about how to figure out which reagents is appropriate to use.

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