The oxidative dimerisation of 1,2,3,4-tetrahydro-6-hydroxy-7-isopropylnaphthalene

Abstract

Periodate oxidation of 1,2,3,4-tetrahydro-6-hydroxy-7-isopropylnaphthalene gives the dimer of the corresponding 6-hydroxycyclohexadienone. Thermolysis of the dimer yields mainly 1,2,3,4-tetrahydro-6,7-dihydroxy-5-isopropylnaphthalene together with some propene and 1,2,3,4-tetrahydro-6,7-dihydroxynaphthalene; the reaction is analogous to the thermolysis of maytenone. The structure of 1,2,3,4-tetrahydro-6,7-dihydroxy-5-isopropylnaphthalene has been confirmed by an independent synthesis.