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Claisen Rearrangement
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The Claisen Rearrangement is a pericyclic reaction (concerted reaction + cyclic transition state) that belongs to the group of sigmatropic reactions (one σ-bond is exchanged to another). A [3,3] sigmatropic rearrangement where an allyl vinyl ether is converted to an unsaturated carbonyl compound. • General features: • 1. The reaction can be also described as a suprafacial, concerted, nonsynchronous [3,3]-sigmatropic rearrangement. • 2. If chiral allylic alcohols are used to prepare the starting allyl vinyl ether, then the chirality is transferred to the products. • Mechanism: • 1. The allylic alcohol reacts with the enol ether to give an allyl vinyl ether. Then, Claisen Rearrangement. • Seminal publications: • 1. Ber. 1913, 45, 3157-3166. https://doi.org/10.1002/cber.19120450348 • 2. Ann. 1914, 401, 21-119. https://doi.org/10.1002/jlac.19134010103 • Similar reactions: • Cope rearrangement: • Cope Rearrangement
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