A one-pot oxone-mediated/iodine-catalyzed
oxidative rearrangement
of stilbenes leading to 2,2-diaryl-2-hydroxyacetaldehydes is described.
Control experiments revealed that a 2,2-diarylacetaldehyde was initially
formed that undergoes subsequent α-hydroxylation. The resulting
α-hydroxyaldehydes have been subjected to a one-pot Still–Gennari
olefination followed by cyclization, leading to 5,5-diaryl-γ-butenolides.