ChemInform Abstract: Synthesis and Reactions of Peroxides of the Enyne Series.

Abstract

ChemInform Abstract Condensation of the 2-methylhexenyn-2-ol (I) with the peroxides (II) yields the enyneperoxides (III) with a conjugated enyne system and a terminal acetylenic bond, a hitherto unknown structure. The peroxide (IIIb), on reaction with acetone (IV) yields the hydroxyperoxide (V), and the peroxide (IIIc) is hydrated at the terminal acetylenic bond to give the ketoperoxide (VI). The compounds (III), (V)and (VI) do not undergo homopolymerization, but they are able to copolymerize as shown by the copolymerization of (IIIa) and (IIIb) with styrene.

Catalytic Hydration of Alkynes and Its Application in Synthesis

“…198 (b) Hydration of a camphor-derived propargyl alcohol gives a useful chiral auxiliary. 58,199 The epoxide of an ethynyl oxirane 209 and also peroxide groups 210 are tolerated in alkyne hydration. Aldehydes can be present in the starting material.…”