Rearrangement of Methylenebis(cyclohexane-1,3-dione) Enols Induced by Mn(III)-Catalyzed Aerobic Oxidation.

ABSTRACT

The Mn(III)-catalyzed aerobic oxidation of methylenebis(cyclohexane-1,3-dione) enols 1 resulted in 6a-hydroxy-2,3,4,6a,7,8,9,10a-octahydro-1H-benzo[c]chromene-1,6,10-triones 3 during the formation of 4,5,8,10,11,12-hexahydro-2H-benzo[b]oxecine-2,6,7,9(3H)-tetraones 2. The mechanism for the formation of 3 was proposed on the basis of the isolation of intermediates 2, which were transformed into 3 under Claisen and retro-Claisen conditions.