O-benzylation of hexahomotrioxacalix[3]arene with benzyl bromide gave tri-O-benzylated products with cone and partial-cone conformation, in a ratio governed by the base used. cone-Tris-O-benzyloxy derivative shows a selectivity for the n-butylammoniun ion.
For a comprehensive review of all aspects of calixarene chemistry, see: (a) GutscheC.D., Calixarenes, Royal Society of Chemistry, Cambridge, 1989; (b) J. Vicens and V. Böhmer, CALIXARENES: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Cambridge, 1990; (c) C.D. Gutsche, Calixarenes Revisited, Royal Society of Chemistry, Cambridge, 1998.
2.
(a) BottS.G., ColemanA.W., and AtwoodJ.L., J. Chem. Soc., Chem. Commun., 1986, 610; (b) A. Anduni, A. Pochini, S. Reverber, R. Ungaro, G.D. Andretti and F. Ugozzoli, Tetrahedron, 1986, 42, 2089.
3.
(a) ArakiK., HashimotoN., OtsukaH., and ShinkaiS., J. Org. Chem., 1993, 58, 5958; (b) K. Araki, K. Inaba, H. Otsuka and S. Shinkai, Tetrahedron, 1993, 49, 9465; (c) M. Takeshita and S. Shinkai, Chem. Lett., 1994, 125; (d) H. Matsumoto, S. Nishio, M. Takeshita and S. Shinkai, Tetrahedron, 1995, 51, 4647; (e) K. Araki, K. Inada and S. Shinkai, Angew. Chem. Int. Ed. Engl., 1996, 35, 72.
4.
(a) NinagawaH., and MatsudaH., Makromol. Chem. Rapid Commun., 1982, 3, 65; (b) B. Dhawan and C.D. Gutsche, J. Org. Chem., 1983, 48, 1536; (c) P.D. Hampton, Z. Bencze, W. Tong and C.E. Daitch, J. Org. Chem., 1994, 59, 4838; (d) C.E. Daitch, P.D. Hampton, E.N. Duesler and T.M. Alam, J. Am. Chem. Soc., 1996, 118, 7769.
5.
(a) YamatoT., HaraguchiM., NishikawaJ., IdeS., and TsuzukiH., Can. J. Chem., 1998, 76, 989; (b) T. Yamato, M. Haraguchi, J. Nishikawa and S. Ide, J. Chem. Soc., Perkin Trans. 1, 1998, 609; (c) T. Yamato and F. Zhang, J. Inclusion Phenom., 2001, 42, 55.
6.
(a) YamatoT., ZhangF., TsuzukiH., and MiuraY., Eur. J. Org. Chem., 2001, 1069; (b) T. Yamato, F. Kitajima and J. Tae Gil, J. Inclusion Phenom., 2005, 53, 257.
7.
BenesiH.A., and HildebrandJ.H., J. Am. Chem. Soc., 1949, 71, 2073.
