The constitution of the dimers of 4,6-di-t-butyl-3-hydroxy-o-benzoquinone and 5-t-butyl-3-hydroxy-o-benzoquinone

Abstract

Evidence is presented which shows that the yellow and white dimers of 4,6-di-t-butyl-3-hydroxy-o-benzoquinone are structures 3,4a,6,8-tetra-t-butyl-4a, 10a-dihydro-9,10a-dihydroxydibenzo-p-dioxin-1,2-dione (II) and 2,3a,5,7-tetra-t-butyl-3a,10a-dihydro-8,10a-dihydroxybenzo[b]cyclopenta[f][1,4]dioxepin-1,10-dione (IV), respectively. The suggested position of substitution of the t-butyl group in 5-t-butylpyrogallol has been confirmed, thus establishing the dimer of 5-t-butyl-3-hydroxy-o-benzoquinone as 5,10-di-t-butyl-2,7-dihydroxytricyclo-[5,3,1,1^2,6]dodeca-4,9-diene-3,8,11,12-tetraone (XIII). In preparing 5-t-butylpyrogallol, a novel sequence of reactions was used to attach the t-butyl group in situ.