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

Mechanism

Original Paper

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Related Compounds