Rupe rearrangement, Meyer-Schuster

Swamlnathan, S., Narayanan, K. V. Rupe and Meyer-Schuster rearrangements. Cherm. Rev. 1971, 71,429-438. 

Andres, J., Silla, E., Tapia, O. A quantum chemical study of protonated intermediates in Rupe and Meyer-Schuster rearrangement mechanisms. THEOCHEM 1983,14, 307-314. 

The products from the acid-catalyzed hydration of a-tertiary alcohols 30 (Meyer-Schuster and Rupe rearrangements) are formed via the mesomeric propargyl-allenyl cation (equation 9) and have been extensively investigated28. 

When 2-ethynyl-2-hydroxyadamantane (31) was treated with 95% formic acid or dilute sulfuric acid only a Meyer-Schuster rearrangement took place to give 95% of 2-(formylmethylene)adamantane (32) (equation 10). No Rupe rearrangement took place29. 

The Meyer-Schuster Rearrangement is similar to the Rupe Rearraneement. 

Although a variety of acid catalysts are employed in the Meyer-Schuster and Rupe rearrangements, formic acid is commonly used to effect the respective transformations. ... 

The practicality of the Meyer-Schuster and Rupe rearrangements has been further demonstrated in synthetic efforts toward insect pheremones. 

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