Journal of the Chemical Society. Perkin transactions I p. 2217 - 2220 (1984)
Update date:2022-08-28
Topics:
Bascetta, Emanuele
Gunstone, Frank D.
The silver trifluoroacetate-assisted reaction of alkyl halides with hydrogen peroxide has been investigated.Methyl 12-bromostearate furnished, for the first time, methyl 12-hydroperoxystearate in 34percent yield.Methyl 12-bromo-oleate, however, gave cyclopropane hydroperoxides (via a homoallylic cation rearrangement) and hydroperoxy epidioxides (presumably via methyl 12-hydroperoxyoleate which could not be isolated).Methyl 9-t-butylperoxy-10,11-methyleneheptadecanoate was produced by the reaction of methyl 12-bromo-oleate with t-butyl hydroperoxide in the presence of silver trifluoroacetate.None of these transformations occurred when silver trifluoroacetate was replaced by the acetate.
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