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Preparation of Propargyl Hydroperoxides by Regioselective Oxidation of Allenic Zinc Reagents with Molecular Oxygen

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journal contribution
posted on 2003-07-25, 00:00 authored by Toshiro Harada, Emiko Kutsuwa
Treatment of allenic zinc reagents (R1R2CCC(R3)ZnL), generated by the reaction of propargyl derivative (R1R2C(X)C⋮CH) with triorganozincates (R33ZnLi), under oxygen atmosphere in the presence of ZnCl2 and chlorotrimethylsilane afforded propargyl hydroperoxides (R1R2C(OOH)C⋮CR3) regioselectively. In this reaction, the use of ZnCl2 and chlorotrimethylsilane as additives is essential for the transformation of the initially generated allenic reagents to more reactive chlorozinc species.

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