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The octaphosphorylation of calix [4]resorcinarenes 1 by 2-dialkylamino-1,3,2-diheterophosphorinanes 2 is described, and the effect of different factors on the structures of the resulting perphosphorylated products 3−5 was studied. Conformation analysis of these compounds by correlated 2D NMR spectroscopy and X-ray diffraction analysis was performed, and it was found that compounds 3−5, like the initial resorcinarenes 1, each have the all-cis configuration of the R groups in the methylidene bridges of the calixarene system, but different orientations of benzene rings and phosphorinane fragments with respect to one another and to the macrocycle plane. Perphosphorylated resorcinarenes 3a−c, 4a and 5a with R = alkyl

Regioselective phosphorylation of rctt tetranaphthyl resorcinarenes gave monofunctionalized derivatives with eight phosphamide groups immobilized on the macrocyclic matrix, as well as heterofunctionalized derivatives containing hydroxyl groups on the vertically oriented benzene rings and phosphorus fragments on the planar benzene rings.

Directed modification of rctt-tetra-C-naphthyl resorcin[4]arene afforded a heterofunctionalized derivative containing specifically oriented phosphoryl and acetyl groups, and its ability to form complexes with organic amines was studied. The structure and stereochemistry of the resulting complexes depended on the amine nature.