A new synthesis of <i>ortho</i>‐Quinones by transition‐metal‐mediated oxygenation of phenols with <i>tert</i>‐butylhydroperoxide and the mimoun oxodiperoxo molybdenum complex [Mo(O₂)₂O] · Py · HMPT

Abstract

Abstract A specific oxygenation of phenols to ortho ‐quinones can be effected by a combination of the transition metal complexes Ti(O i Pr) 4 , VO(acac) 2 , Zr(acac) 4 , Zr(O n Pr) 4 and tert ‐butylhydroperoxide (TBHP) or [Mo(O 2 ) 2 O] · Py · HMPT. Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phenols are readily converted into the corresponding 1,2‐quinones. Unhindered ortho ‐naphthoquinones can yield binaphthyls with unreacted starting material by Michael addition.