Synthesis of Partially Bridged Phosphonate and Thiophosphonate Resorcinarenes

Abstract

The synthesis of partially bridged thiophosphonate and phosphonate resorcinarenes is reported in this paper. Resorcinarenes functionalised at the upper rim with two or three P = X (X = S,O) bridges oriented towards the molecular cavity are obtained from the treatment of the corresponding (iiii) tetrasubstituted cavitand with 1,2-dihydroxybenzene and base in DMF. This synthetic route selectively promoted the formation of one of the two disubstituted resorcinarenes, the AC isomer. The crystal structure of the AC-dithiophosphonated resorcinarene 4 has been determined.

Keywords:

• Thiophosphonated resorcinarenes
• Phosphonated resorcinarenes
• Partially bridged cavitands
• 1,2-dihydroxybenzene

Acknowledgements

This work was supported by MUR (Ministero Universìtá e Ricerca) through PRIN 2005 (Progetti di ìnteresse nazìonale). The instrumentation facilities at the Centro Interfacoltà Misure G. Casnati of the University of Parma were used.

Notes

¹ The crystal structure of a relevant AC dithiophosphonate resoncinarene with undecyl feet has been reported by Dutasta's group.