Synthesis of the parent resorcin[4]arene

Abstract

The treatment of 2,4-bis(allyloxy)benzyl alcohols with Sc(OTf )₃ in acetonitrile produced a cyclic tetramer as the major product, which was deallylated by ammonium formate and PdCl₂(PPh₃)₂ to produce the parent resorcin[4]arene.

References

1. P. Timmerman, W. Verboom and D. N. Reinhoudt, Tetrahedron, 1996, 52, 2663.
2. D. J. Cram and J. M. Cram, Container Molecules and Their Guests, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge, 1994.
3. V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
4. C. D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge, 1989.
5. A. G. S. Högberg, J. Am. Chem. Soc., 1980, 102, 6046.
6. A. G. S. Högberg, J. Org. Chem., 1980, 45, 4498.
7. H. Konishi, T. Nakamura, K. Ohata, K. Kobayashi and O. Morikawa, Tetrahedron Lett., 1996, 37, 7383.
8. M. F. Olusegun, E. Al-Farhan, P. M. Keehn and R. Steveson, Tetrahedron Lett., 1994, 35, 65.
9. O. Haba, K. Haga, M. Ueda, O. Morikawa and H. Konishi, Chem. Mater., 1999, 11, 427.
10. T. Tsuchimoto, K. Tobita, T. Hiyama and S. Fukuzawa, J. Org. Chem., 1997, 62, 6997.
11. S. Kobayashi, Synlett, 1994, 689.
12. J. Tsuji and T. Yamakawa, Tetrahedron Lett., 1979, 20, 613.
13. C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto and C. J. Sanchez, J. Org. Chem., 1991, 56, 3372.