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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.

Oxidative Rearrangement of Stilbenes to 2,2-Diaryl-2-hydroxyacetaldehydes