Abstract
p-tert-Butylcalix[6]-1,4-2,5-biscrown-4 (2a) is a typical member of the family of calix[6]biscrowns. In the literature, 2a has been prepared in a two-step procedure, the total yield being less than 26.4% and the work-up was troublesome. Herein we wish to report an improved method to synthesize such a compound in one step with a yield of up to 63%. Furthermore, this method could provide a monosubstituted p-tert-butylcalix[6]-1,4-crown-4 (2b) as a by-product. Varying the reaction conditions, we could obtain 2b as a main product with a 48% yield.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
C.D. Gutsche : in J.F. Stoddart (ed.), Calixarenes, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge, (1989)
Z. Asari, V. Bohmer, J. Harrowfield, and J. Vicens: Kluwer Academic Publishers, 2001; V. Bohmer, Angew. Chem, Int. Ed. Engl., 34, 713, (1995)
E. Ghidini F. Ugozzoli V. Retal (1990) J. Am. Chem. Soc 112 697 Occurrence Handle10.1021/ja00175a035
A. Casnati N.D. Ca F. Sansone F. Ugozzoli R. Ungaro (2004) Tetrahedron 60 7869 Occurrence Handle10.1016/j.tet.2004.06.058 Occurrence Handle1:CAS:528:DC%2BD2cXmsVajtrs%3D
J.-F. Dozol, V. Lamare, N. Simon, R. Ungaro, and A. Casnati: in G.J. Lumetta, R.D. Rogers, A.S. Gopalan, (eds.), Calixarene Molecules for Separation, J. Am. Chem. Soc. 12, (2000)
A. Casnati A. Pochini R. Ungaro F. Ugozzoli F. Arnaud S. Fanni M.-J. Schwing R.J.M. Egberink F.D. Jong D.N. Reinhoudt (1995) J. Am. Chem. Soc 117 2767 Occurrence Handle10.1021/ja00115a012 Occurrence Handle1:CAS:528:DyaK2MXktFeiu7s%3D
H.F. Ji R. Dabestani G.M. Brown R.A. Sachleben (2000) Chem. Commun 10 833
J.S. Kim W.K. Lee I.H. Suh J.G. Kim J. Yoon J.H. Lee (2000) J. Org. Chem 65 7215 Occurrence Handle1:CAS:528:DC%2BD3cXms1Olur8%3D
P. Thuery M. Nierlich E. Lamare J.F. Dozol Z. Asfari J. Vicens (2000) J. Incl. Phenom 36 375 Occurrence Handle1:CAS:528:DC%2BD3cXivFSnurg%3D
A. Casnati P. Jawpozzi A. Pochini F. Ugozzoli R. Caceiapaglia L. Mandolini R. Ungaro (1995) Tetrahedron 51 591 Occurrence Handle1:CAS:528:DyaK2MXjtlKisLc%3D
J.S. Li Y.Y. Chen X.R. Lu (1999) Tetrahedron 55 10365 Occurrence Handle1:CAS:528:DyaK1MXlsVylur4%3D
(a) Y.Y. Chen, F.F. Yang, and X.R. Lu: Tetrahedron Lett. 41, 1571 (2000); (b) Y.Y. Chen, F.F. Yang, P. Thuéry, M. Nierlich, and J.Vicens: J. Incl. Phenom., 42, 261 (2002)
Y.K. Chen Y.Y. Chen (2000) Org. Lett 2 743 Occurrence Handle1:CAS:528:DC%2BD3cXhtlOqsr8%3D
M.T. Blanda D.B. Farmer J.S. Brodbelt B.J. Goolsby (2000) J. Am. Chem. Soc 122 1486 Occurrence Handle10.1021/ja991810h Occurrence Handle1:CAS:528:DC%2BD3cXns1Kisg%3D%3D
(a) Y.Y. Chen and H.B. Li: Chem. Lett. 1208 (2000); (b) Y.Y. Chen and H.B. Li: New J. Chem. 25, 340 (2001)
(a) S.W. Ko, Y.S. Yang, J.H. Mun, K.-M. Park, S.S. Lee, and K.C. Nam: Bull. Korean. Chem. Soc. 23, 1379 (2002); (b) S.W. Ko, B.J. Ryu, K.-M. Park, K.H. No, J.S. Kim, and K.C. Nam: Bull. Korean. Chem. Soc. 25, 957 (2004)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Guan, B., Gong, S., Wu, X. et al. One-step Synthesis of p-tert-Butylcalix[6]-1,4-2,5- biscrown-4 and its Tosyloxyethoxyethylate Derivative. J Incl Phenom Macrocycl Chem 54, 81–84 (2006). https://doi.org/10.1007/s10847-005-4601-3
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s10847-005-4601-3