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26.9.1.1.22 Method 22: Isomerization of Propargylic Alcohols

DOI: 10.1055/sos-SD-026-00987

Marsden, S. P.Science of Synthesis, (2005261103.

Propargylic alcohols can be rearranged to enones to give one of two regiochemical outcomes.[‌261‌] The Rupe rearrangement is believed to proceed through elimination of water followed by regioselective hydration of the alkyne, giving the rearranged enone 340 (Scheme 58). The MeyerSchuster rearrangement proceeds by interception of a propargylic cation, leading to transposition of the oxygen and hence enones of the type 341.

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