Abstract
Oxidation of allyl phenyl selenides with m-chloroperbenzoic acids(mCPBA) afforded addition products of m-chlorobenzoic acid(mCBA) and diols rather than allyl alcohols. In order to investigate the mechanism of formation of these products, the oxidation reaction was carried out under various conditions. The oxidation with tBuOOH or with mCPBA in the presence of triethylamine gave the corresponding allyl alcohols, while that with tBuOOH in the presence of mCBA gave the addition products. The reactions were also carried out with purified mCPBA in the absence or presence of water to observe the distribution of diol products. These results reveal that the oxidation under acidic and neutral conditions produces addition products and allyl alchohols, respectively. The presence of a significant amount of water is important in the formation of the diols.
