Rearrangement on oxidation of dialkylacetylenes

Franzen170 observed that when dialkylacetylenes are oxidized by peracetic acid a rearrangement to give dialkylacetic acids accompanies cleavage of the triple bonds, e.g  

This reaction is somewhat analogous to the Wolff-Schroter rearrangement (see below). 

Hiickel, Theoretische Grundlagen der organischen Chemie, 7th ed., Akad. VerlagsGes. Geest and Portig K.-G., Leipzig, 1952, Vol. 1, p. 369. 

5-Decyne (20 g) is treated with a 12% solution of peracetic acid (3 molar equivalents) in glacial acetic acid. The mixture is set aside for 10 days, initially with cooling. After removal of the acetic acid in a vacuum, the residue is esterified with methanol and hydrogen chloride. Fractionation then affords a fraction, b.p. 90°/9 mm, which on alkaline hydrolysis gives 2-butylhexanoic acid (12 g, 54%), b.p. 137°/12 mm. 

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