Meyer-Schuster rearrangement

What is Meyer-Schuster rearrangement?

The Meyer-Schuster rearrangement is a reaction that is catalyzed by acid and involves the rearrangement of secondary and tertiary α-acetylenic alcohols to α,β-unsaturated carbonyl compounds. The Meyer-Schuster rearrangement leads to the formation of aldehydes when the acetylenic group is terminal, and ketones when it is internal.

Meyer-Schuster rearrangement
Meyer-Schuster rearrangement

In 1926, a rearrangement closely related to the Meyer-Schuster rearrangement was described and named the Rupe rearrangement. The Rupe rearrangement involves the conversion of tertiary alkylacetylenic carbinols with a terminal acetylenic group into predominantly α,β-unsaturated ketones, rather than the expected aldehydes.

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