N- and O-arylation with triphenylantimony ortho-phenylenedioxides

2,2,2-Triphenyl-1,3,2-benzodioxastibolanes react with alcohols, phenols, and amines in the presence of copper salts to give the corresponding O- and N-phenyl derivatives. Cyclic Sb-V dialkoxide containing an electron-withdrawing nitro group in the dioxastibolane fragment is most reactive in N-phenylation of primary and secondary amines. Organoantimony analogs containing electron-donating groups are more efficient in O-phenylation of primary and secondary alcohols and phenols.