Lead tetraacetate (LTA) oxidation of the allylic alcohols1, 10, 14and19leads to the formation of the epoxides2, 11, 15and20, products of a novel internal addition reaction of the electron deficient alcohol oxygen to the allylic double bond. In some cases (10, 14) the formation of a new type of acetoxylated enolethers (12, 16) is observed. The LTA oxidation of the allylic dienols21and29gives rise to the formation of the epoxyacetates25and33, products of a similar internal addition reaction. Furthermore, a variety of cyclization products (22, 23, 24, 26, 30, 31, 32and34) has been isolated whose formation requires an isomerisation of the allylictransdouble bond to acisone.
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Ehrenfreund et al. (1974) studied this question.
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