The thermal [3,3]-sigmatropic rearrangement of 1,5-dienes to the isomeric form is known as the Cope rearrangement, which can only be detected when the 1,5-diene substrate is substituted. As a reversible reaction, the forward direction is favored when the product is stabilized by conjugation or the resulting double bond is more highly substituted. A chair-like transition state renders the reaction both stereospecific and stereoselective, favoring least steric interactions between substituents.

  • Reactant: 1,5-Diene
  • Product: 1,5-Diene
  • Type of Reaction: [3,3]-Sigmatropic Rearrangement


Top Citations

Original Paper

Related Reactions

  • Claisen Rearrangement
  • Overman Rearrangement

Related Compounds

  • 1,5-Diene (CAS 592-42-7)
By shuhan yang


Just added to your wishlist:
My Wishlist
You've just added this product to the cart:
Go to cart page