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Meyer-Schuster Rearrangement; Rupe Rearrangement

Acid-catalyzed rearrangement of secondary and tertiary α-acetylenic alcohols to α,β-unsaturated carbonyl compounds; aldehydes result when the acetylenic group is terminal, ketones when it is internal:

Meyer-Schuster Rearrangement; Rupe Rearrangement

The conversion of tertiary alkylacetylenic carbinols with a terminal acetylenic group to predominantly α,β-unsaturated ketones, not the expected aldehydes, is referred to as the Rupe rearrangement:

Meyer-Schuster Rearrangement; Rupe Rearrangement

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