O-Alkylation of the flexible tetrahomodioxacalix[4]arene 1 with N,N-diethylchloroacetamide in the presence of NaH, K2CO3 or Cs2CO3 gave only one pure stereoisomer, 1,4-alternate-2, while other possible isomers were not observed.
(a) For a comprehensive review of all aspects of calixarene chemistry, see: 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) ShinkaiS., Tetrahedron, 1993, 49, 8933; (b) V. Böhmer, Angew. Chem. Int. Ed. Engl., 1995, 34, 713; (c) M. Takeshita and S. Shinkai, Bull. Chem. Soc. Jpn., 1995, 68, 1088; (d) A. Ikeda and S. Shinkai, Chem. Rev., 1997, 97, 1713.
3.
(a) ArimuraT., KubotaM., MatsudaT., ManabeO., and ShinkaiS., Bull. Chem. Soc. Jpn., 1989, 62, 1674; (b) S. Shinkai, K. Fujimoto, T. Otsuka and H.L. Ammon, J. Org. Chem., 1992, 57, 1516.
4.
(a) IwamotoK., and ShinkaiS., J. Org. Chem., 1992, 57, 7066; (b) K. Iwamoto, K. Araki and S. Shinkai, J. Chem. Soc., Perkin Trans. 1, 1991, 1611; (c) C.D. Gutsche and P.A. Reddy, J. Org. Chem., 1991, 56, 4783.
5.
(a) van LoonJ.D., GroenenL.C., WijmengaS.S., VerboomW., and ReinhoudtD.N., J. Am. Chem. Soc., 1991, 113, 2378; (b) L.C. Groenen, J.D. van Loon, W. Verboom, S. Harkema, A. Casnati, R. Ungaro, A. Pochini, F. Ugozzoli and D.N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 2385; (c) K. Fujimoto, N. Nishiyama, H. Tsuzuki and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1992, 643; (d) K. Iwamoto, K. Araki and S. Shinkai, Tetrahedron, 1991, 47, 4325.
6.
MasciB., PersianiD., and ThuéryP., J. Org. Chem., 2006, 71, 504.
7.
(a) ArduiniA., GhidiniE., PochiniA., UngaroR., AndreettiG.D., CalestaniG., and UgozzoliF., J. Incl. Phenom., 1988, 6, 119; (b) H. Matsumoto, S. Nishio, M. Takeshita and S. Shinkai, Tetrahedron, 1995, 51, 4647.
8.
(a) YamatoT., SaruwatariY., NagayamaS., MaedaK., and TashiroM., J. Chem. Soc., Chem. Commun., 1992, 861; (b) T. Yamato, Y. Saruwatari and M. Yasumatsu, J. Chem. Soc., Perkin Trans. 1, 1997, 1725; (c) T. Yamato, Y. Saruwatari and M. Yasumatsu, J. Chem. Soc., Perkin Trans. 1, 1997, 1731; (d) T. Yamato, M. Haraguchi, T. Iwasa and H. Tsuzuki: Anales Quím. Int. Ed., 1997, 93, 301; (e) T. Yamato, Y. Saruwatari, M. Yasumatsu and S. Ide, Eur. J. Org. Chem., 1998, 309.
9.
(a) Arnaud-NeuF., CreminS., CunninghamD., HarrisS.J., McArdleP., McKerveyM.A., McManusM., Schwing-WeillM.J., ZiatK., J. Inclusion Phenom., 1991, 10, 329; (b) B. Masci, S.L. Mortera, D. Persiani and P. Thuéry, J, Org. Chem., 2006, 71, 505.
10.
(a) JaimeC., de MendozaJ., PradosP., NietoP.M., and SánchezC., J. Org. Chem., 1991, 56, 3372; (b) J.O. Magrans, J. de Mendoza, M. Pons and P. Prados, J. Org. Chem., 1997, 62, 4518.
11.
(a) KeehnP.M., and RosenfieldS.M. (eds), Cyclophanes, Academic Press: New York, vol. 1&2, 1983; (b) F. Vögtle, Cyclophane-Chemistry, Wiley: Chichester, 1993.
12.
InokumaS., YasudaS., ArakiS., SakaiS., and NishimuraJ., Chem. Lett., 1994, 201.
13.
(a) AsfariZ., AbidiR., ArnaudF., and VicensJ., J. Incl. Phenom., 1992, 13, 163; (b) F. Ohseto and S. Shinkai, Chem. Lett., 1993, 2045.
14.
(a) KanamathareddyS., and GutscheC.D., J. Org. Chem., 1992, 57, 2160; (b) F. Cunsolo, M. Piattelli and P. Neti, J. Chem. Soc., Chem. Commun., 1994, 1977.
15.
DhawanB., and GutscheC.D., J. Org. Chem., 1983, 48, 1536.