Regiodirected phosphorylation of 2,2′,7,7′-tetrahydroxydinaphthylmethane

The phosphorylation of 2,2′,7,7′-tetrahydroxydinaphthylmethane was studied and the influence of molecule pre-organization on the regioselectivity of functionalization was investigated. The reactions of 2,2′,7,7′-tetrahydroxydinaphthylmethane with phosphorous amides containing 1–3 amide bonds gave oligophosphorylated derivatives differing in the number and the nature of phosphorus fragments and in the size of phosphorus rings: tetraphosphorus macrocycles containing one 24-membered and two eight-membered phosphorus rings, triphosphorus compounds containing a phosphocine ring and two acyclic phosphorus fragments, and tetraphosphorylated derivatives with four phosphorus groups in the molecule. The possibility of controlling the regioselectivity of phosphorylation by using reagents differing in the number and activity of P–N bonds was demonstrated.