Naturally occurring quinones. Part IX. The chemistry of hydroxyperezone and perezinone

Abstract

(±)-Dihydroperezone, 2-(1,5-dimethylhexyl)-3-hydroxy-5-methyl-1,4-benzoquinone, has been synthesised and the structure of hydroxyperezone “hydrate,” 2,5-dihydroxy-3-(5-hydroxy-1,5-dimethylhexyl)-6-methyl-1,4-benzoquinone, confirmed. Perezinone, the cyclodehydration product from hydroxyperezone, has been shown to have a naphthofuranone structure; it readily autoxidises to give first a conjugated dione and then a dimer which is present on the surface of old samples of perezinone. The dione is converted into the dimer on heating.