Synthesis of a Sulfur-bridged Calixarene

Abstract

A thiacalix[4]arene was obtained by the reaction of the 2,5-thiophene dianion with SCl₂; the analogous reactions of dianions of diaryl thioethers did not yield macrocyclic structures and under the applied conditions diaryl sulfones were further deprotonated and the structure of the fourfold Me₃Si adduct 11 determined by X-ray crystallography.

References

1. B. König, M. Rödel, P. Bubenitschek and P. G. Jones, Angew. Chem., 1995, 107, 752; Angew. Chem., Int. Ed. Engl., 1995, 34, 661; B. König, M. Rödel, P. Bubenitschek, P. G. Jones and I. Thondorf, J. Org. Chem., 1995, 60, 7406.
2. E. Jones and I. M. Moodie, Tetrahedron, 1965, 21, 2413.
3. L. Brandsma, Preparative Polar Organometallic Chemistry 1, Springer, Berlin, 1990; B. J. Wakefield, Organolithium Methods, Academic Press, London, 1988.
4. G. M. Sheldrick, SHELX-93, Program for Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1993.