Regioselective Synthesis and Structure of New Oligophosphorylated rctt Resorcinarenes

Abstract

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.

GRAPHICAL ABSTRACT

Keywords:

• Oligophosphorylation
• oxidation
• phosphorous amides
• regioselectivity
• resorcinarenes
• structure

Acknowledgments

The work was supported in part by RFBR (grant no. 09-03-00201a).

Notes

Crystal data and structure refinement parameters for previously synthesized 3b have been reported. ¹²

Compound 7 was synthesized previously by direct octaphosphorilation of resorcinarene 1b.

Compounds 5 and 10 exhibited an extremely poor solubility in most organic solvents, and so an extended study of their ¹³C NMR spectra could not be performed.