Preparation of propargyl hydroperoxides by regioselective oxidation of allenic zinc reagents with molecular oxygen.
Treatment of allenic zinc reagents (R(1)R(2)C[double bond]C[double bond]C(R(3))ZnL), generated by the reaction of propargyl derivative (R(1)R(2)C(X)[triple bond](CH) with triorganozincates (R(3)(3)ZnLi), under oxygen atmosphere in the presence of ZnCl(2) and chlorotrimethylsilane afforded propargyl hydroperoxides (R(1)R(2)C(OOH)C[triple bond];CR(3)) regioselectively. In this reaction, the use of ZnCl(2) and chlorotrimethylsilane as additives is essential for the transformation of the initially generated allenic reagents to more reactive chlorozinc species.
Harada
Toshiro
T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. harada@chem.kit.ac.jp
Kutsuwa
Emiko
E