Abstract
We have synthesized novel calix[4]resorcinols with four 2-thioxo-1,3,2-dioxaphospholane groups introduced in aromatic substituents in the methylidene bridges of macromolecules by the condensation of new thiophosphorylated benzaldehyde with resorcinol and its derivatives in acidic media with high yields. The formation of only one rctt isomer with corresponding chair conformation is observed, which was determined by 2D NMR-experiments.
References
Jain, V.K., Kanaiya, P.H.: Chemistry of calyx[4]resorcinarenes. Russ. Chem. Rev. 80, 75–102 (2011)
Tunstad, L.M., Tucker, J.A., Dalcanale, E., Weiser, J., Bryant, J.A., Sherman, J.C., Helgeson, R.C., Knobler, C.B., Cram, D.J.: Host–guest complexation. 48. Octol building blocks for carcerands and cavitands. J. Org. Chem. 54, 1305–1312 (1989)
Thoden van Velzen, E.U., Engbersen, J.F., Reinhoudt, D.N.: Self-assembled monolayers of receptor adsorbates on gold: preparation and characterization. J. Am. Chem. Soc. 116, 3597–3598 (1994)
Högberg, A.G.S.: Two stereoisomeric resorcinol-acetaldehydes condensation product. J. Org. Chem. 45, 4498–4500 (1980)
Yamakawa, Y., Ueda, M., Nagahata, R., Takeuchi, T., Asai, M.: Rapid synthesis of dendrimers based on calix[4]resorcinarenes. J. Chem. Soc. Perkin Trans. 1, 4135–4139 (1998)
Prosvirkin, A.V., Kazakova, E.K., Gubaidullin, A.T., Litvinov, I.A., Gruner, M., Habicher, W.D., Konovalov, A.I.: Synthesis of rctt, rccc, and rcct diastereomers of calix[4]methylresorcinarenes based on p-tolualdehyde. X-ray diffraction study of the rcct isomer. Formation of rctt and rccc cavitands in a cone conformation. Russ. Chem. Bull. Int. Ed. 54, 2550–2557 (2005)
Gavrilova, E.L., Naumova, A.A., Shatalova, N.I., Burilov, A.R., Pudovik, M.A., Krasilnikova, E.A., Konovalov, A.I.: The new type of calix[4]resorcines bearing phosphonates and phosphonium fragments at the lower rim. Phosphorus Sulfur Silicon Relat. Elem. 183, 561–565 (2008)
Da Costa, C.P., Krajewska, D., Okruszek, A., Stec, W.J., Sigel, H.: Stabilities of lead(II) complexes formed in aqueous solution with methyl thiophosphate (MeOPS2−), uridine 5′-O-thiomonophosphate (UMPS2−) or adenosine 5′-O-thiomonophosphate (AMPS2−). J. Biol. Inorg. Chem. 7, 405–415 (2002)
Mikulski, C.M., Chaudan, S., Rabin, R., Karayannis, N.M.: Well-defined adducts of triethyl thiophosphate with some metal perchlorates. J. Inorg. Nucl. Chem. 43, 2017–2020 (1981)
Wang, H., Li, Zh, Liu, Y.: Synthesis and cationic selectivity studies of novel calix[4]arene derivatives containing heteroatom at the lower rim. Sci. China Ser. B Chem. 50, 654–659 (2007)
Knyazeva, I.R., Burilov, A.R., Fazleeva, G.M., Nuretdinov, I.A., Gryaznova, T.V., Budnikova, Y.G., Khrisanforova, V.V., Gubaidullin, A.T., Gabidullin, B.M., Syakaev, V.V., Pudovik, M.A., Konovalov, A.I.: New calix[4]resorcinols with thiophosphoryl-containing fragments. Phosphorus Sulfur Silicon Relat. Elem. 186, 1972–1980 (2011)
Maslennikova, V.I., Serkova, O.S., Gruner, M., Goutal, S., Bauer, I., Habicher, W.D., Lyssenko, K.A., Antipin, M.Y., Nifantyev, E.E.: Synthesis and conformation analysis of new phosphorylated calix[4]resorcinarenes. Eur. J. Org. Chem. 23, 4884–4893 (2004)
Bibal, B., Declercq, J.-P., Dutasta, J.-P., Tinantb, B., Valad, A.-G.: Thiophosphorylated cavitand: structure and affinity towards soft metal ions. Tetrahedron 59, 5849–5854 (2003)
Sheldrick, G.M.: SHELXTL v.6.12, structure determination software suite. Bruker AXS, Madison (2000)
Farrugia, L.J.: WinGX suite for small-molecule single-crystal crystallography. J. Appl. Cryst. 32, 837–838 (1999)
Spek, A.L.: Single-crystal structure validation with the program PLATON. J. Appl. Cryst. 36, 7–13 (2003)
Yamasaki, T., Sato, T.: Heterocyclic compounds containing phosphorus. I: on the syntheses of five membered monothio phosphates. Sci. Rep. Res. Inst. Tohoku Univ. Ser. A 6, 384 (1954)
Acknowledgments
The work was supported by the Russian Foundation for Basic Research (grant 11-03-00416-a) and DAAD (Deutscher Akademischer Austauschdienst).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Knyazeva, I.R., Sokolova, V.I., Gruner, M. et al. Single step preparation and conformational analysis of novel thiophosphorylated ligands based on calix[4]resorcinol matrix. J Incl Phenom Macrocycl Chem 76, 231–235 (2013). https://doi.org/10.1007/s10847-012-0190-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-012-0190-0