Claisen Rearrangement: [3,3]-Sigmatropic Shift (Allyl Vinyl/Aryl Ethers → Carbonyl Products)

Learn the Claisen rearrangement: concerted [3,3] shift, chair transition state, and why it's stereospecific. Predict products for allyl vinyl/aryl ethers.

  • Reaction: Allyl vinyl ether → γ,δ-unsaturated carbonyl (after tautomerization)
  • What it does: Rearranges allyl ethers via pericyclic shift
  • Typical reagents: Heat
  • Key intermediate: None (concerted transition state)
  • Driving force: Formation of new C–C bond; tautomerization to carbonyl
  • Exam type: Pericyclic
  • Exam type: Stereospecificity

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