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47.1.3.3.3 Method 3: Cope Rearrangement

DOI: 10.1055/sos-SD-047-00309

Lu, J.-M.; Shao, L.-X.; Shi, M.Science of Synthesis, (201047763.

The thermal [3,3]-sigmatropic rearrangement of 1,5-dienes to isomeric 1,5-dienes is called the Cope rearrangement, and it is only observable when the 1,5-diene substrate is appropriately substituted (Scheme 10).[‌19‌] The rearrangement is reversible because there are no changes in the numbers or types of bonds, and the position of the equilibrium is determined by the relative stabilities of the starting material and the product. When the product is stabilized by conjugation or the resulting double bond is more highly substituted, the equilibrium position will be shifted toward the formation of the product. The reaction is both stereospecific and stereoselective as a result of a cyclic chair-like transition state.

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