4β-Acetoxy-1,2-dihydrosantonene (IIb), which can be prepared by oxidation of 1,2-dihydrosantonene 3-acetate (I), rearranges with acetic anhydride–pyridine to afford 2β-acetoxy-1,2-dihydrosantonene 3-acetate (IVb) by a mechanism involving intramolecular transfer of the 4β-acetate to the 2-position of the enolic form of (IIb).
P. S. Aumeer and T. B. H. McMurry, J. Chem. Soc. D, 1971, 641 DOI: 10.1039/C29710000641
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