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. 2009 Jun 16;284(33):22087–22098. doi: 10.1074/jbc.M109.013151

FIGURE 9.

FIGURE 9.

Radical and ionic pathways to allene oxide and epoxyalcohol. After homolytic hydroperoxide cleavage and formation of the epoxyallylic radical (top), the subsequent diverging transformations can be represented as radical reactions (blue), or as ionic via a carbocation intermediate (red). The incorporation of oxygen from water in the epoxyalcohol product supports the existence of the carbocation, the intermediate that best accounts for the chemistry of allene oxide synthesis (22).