Dienone- Rearrangement

K. von Auwers, K. Ziegler, Ann. 425, 217 (1921).

Transformation of a 4,4-disubstituted cyclohexadienone into a 3,4-disubstituted phenol upon acid treatment:



Reviews: C. J. Collins, et al., in The Chemistry of the yl Group, S. Patai, Ed. (Interscience, New York, 1966) pp 775-778; A. J. Waring, Adv. Alicyclic Chem. 1, 207 (1967); B. Miller in Mechanisms of Molecular Migrations vol. 1, B. S. Thyagarajan, Ed. (Interscience, New York, 1968) pp 275-285; B. Miller, Accts. Chem. Res. 8, 277 (1975). Mechanism: G. Goodyear, A. J. Waring, J. Chem. Soc. Perkin Trans. II 1990, 103. Steric effects: A. G. Schultz, N. J. Green, Am. Chem. Soc. 114, 1824 (1992); A. A. Frimer et al., J. Org. Chem. 59, 1831 (1994). Synthetic applications: D. J. Hart et al., Tetrahedron 48, 8179 (1992); R. W. Draper et al., Steroids 63, 135 (1998).