Chemoselectivity of reactions of 3,6-di-tert-butyl-1,2-benzoquinone with phosphorylated derivatives of pyrogallol and oxyhydroquinone

Phosphorylated derivatives of pyrogallol and oxyhydroquinone containing two phosphorus atoms, one of which is in the trivalent three-coordinate state, undergo [1+4]-cycloaddition with 3,6-di-tert-butylbenzo-1,2-quinone under mild conditions to form phosphoranes of different nature. Diphosphorus-containing compounds, in which the phosphorus atoms are in different coordination states, were obtained. The presence of halophosphorane moieties in the starting compounds does not prevent the reaction from proceeding quantitatively under mild conditions via the cycloaddition.