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The ability of acetylenic systems to participate in intramolecular reactions proceeding via six-membered cyclic transition states has been established by thermolyses of a number of substituted /3-hydroxyacetylenes, in both the vapor and the liquid states. Thermolyses products consisted solely of those alienes and carbonyl compounds derivable from a 1,5-hydrogen transfer. The homogeneous reactions followed the first-order rate law. Activation energies with a variety of alkyl substituents were essentially within experimental error.

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