Dienone-pheno1 rearrangement studies. 5-Hydroxy-4a-methyl-5,6,7,8-tetra-hydronaphthalen-2(4aH)-one and 5-Acetoxy-4a-methyl-5,6,7,8-tetrahydronaphthalen-2(4aH)-one

Abstract

Attempted synthesis of the first of the title compounds indicates that it undergoes a spontaneous dienone-phenol rearrangement involving ring opening to yield 4-methyl-5,6,7,8-tetrahydronephthalene-l,8-diol the structure of which has been confirmed by an unambiguous synthesis of its Ar-methyl ether. The second of the title compounds has been synthesized and undergoes an acid-catalysed dienone-phenol rearrangement in acetic anhydride to yield a ring-opened aldehyde diacetate, the structure of which has been confirmed by hydrolysis and methylation to the same methyl ether above.