32. A Simple Alkylative 1,2-Carbonyl Transposition of Cyclohexenones
    Oppolzer, W.; Sarkar, T.; Mahalanabis, K. K.
    Helv. Chim. Acta 1976, 59, 2012-2020

Acid catalysed dehydration of the diols 5, derived from the cyclohexenone 3 affords mixtures of 8 and 11. The product ratio 8/11, although strongly dependent on both the reaction conditions and the substituent R, is independent of the diol configuration; this indicates a cationic intermediate 6. Conditions were found, which allow the sequence A → B → C → D (Scheme 2) to be applied to the syntheses of the enones 8, 21 and 25 in fair to good yields from the corresponding cyclohexenones 3, 18 and 22.

DOI : 10.1002/hlca.19760590614