Synthesis of 3,4-dihydro-3,3,8a-trimethylnaphthalene-1,6(2H,8aH)-dione, a 4-acylcyclohexa-2,5-dienone

Abstract

The synthesis is reported of the first simple geminal acyl-substituted cyclohexadienone, which is shown to undergo very easy deacylation with formation of a phenolic ring; similar cleavage, or a formal retro-Fries rearrangement, have so far prevented isolation of the analogous 4-acetyl-4-methylcyclohexa-2,5-dienone.