An Uniformly Occuring Aliphatic Benzil-Benzilic-Acid-Type Rearrangement

Article abstract of DOI:10.1002/hlca.19860690721

Treatment of 6-bromo-2,2,5,5-tetramethylcyclohex-3-enone (2) with aqueous alkaline and air affords 1-hydroxy-2,2,5,5-tetramethylcyclopent-3-enecarboxylic acid (8) as the major product of a benzil-benzilic-acid-type rearrangement.The key compound is 2,2,5,5-tetramethylcyclohex-3-ene-1,2-dione (11).The by-product of the reaction is (E)-2,2,5,5-tetramethylhex-3-enedioic acid (9) as the result of an oxidative cleavage of the 6-membered ring and the isomerization of the double bond.