Schenck rearrangement

The allylperoxystannanes, like the allyl hydroperoxides, undergo the Schenck and Smith allylic rearrangements as illustrated in equation 14-87 for cholesterol derivatives.146 147 The rearrangements of the hydroperoxides are well established to be radical chain reactions 148,149 the rearrangements of the tin derivatives are inhibited by phenols, and it is assumed that they also proceed by a radical chain mechanism as illustrated for the Schenck rearrangement in Scheme 14-7.150 151 It will be noted that the mechanism... 

In allylperoxyl radicals, allylic rearrangement leads to the 1,3-migration of the peroxyl function, with the corresponding shift of the double bond [reaction (28) Schenck et al. 1958],... 

The photooxygenation of furans was investigated initially by Schenck in the mid-forties. A crystalline and highly explosive material 32 was isolated from the parent furan by Schenck and Koch. This secondary ozonide rearranges thermally to an epoxybutanolide and a fcis-epoxide reduction with triphenylphos-phine leads to maleic dialdehyde, methanolysis to a methoxy butenolide. 

---