Synthesis of Nitrogen-, Oxygen- and Sulphur-containing Tripodal Ligands with a Trimethylbenzene CoreC
DOI:
https://doi.org/10.29356/jmcs.v55i3.816Keywords:
1, 3, 5-tris(bromomethyl)benzene, ethyl-xanthate, tris-thiol, tripodal ligands, Michael additions, ligand design.Abstract
Synthetic procedures for the preparation of various nitrogen-,oxygen- and sulphur-containing tripodal ligands having a 1,3,5-
trimethylbenzene core are reported.
Downloads
References
Hennrich, G.; Anslyn, E. V. Chem. Eur. J. 2002, 8, 2219-2224.
Lehn, J.-M. Supramolecular Reactivity and Catalysis of Phosphoryl Transfer. In Bioorganic Chemistry in Healthcare and Technology; Pandit, U. K., Alderweireldt, F. C., Eds.; Plenum Press: New York, 1991.
a) Snyder, L. R.; Glajch, J. L.; Kirkland, J. J. Practical HPLC Method Development; Wiley & Sons: New York, 1988. b) Schmidtchen, F. P. Nachr. Chem. Tech. Lab. 1988, 36, 8-12.
a) Yang, X.; Knobler, C. B.; Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1991, 30, 1507?1508. b) Arunachalam, M.; Ghosh, P. Inorg. Chem. 2010, 49, 943-951. c) Singh, A. S.; Chen, B. Y.; Wen, Y.-S.; Tsai, C.; Sun, S.-S. Org. Lett. 2009, 11, 1867-1870.
d) Lakshminarayanan, P. S.; Ravikumar, I.; Suresh, E.; Ghosh, P. Inorg. Chem. 2007, 46, 4769-4771. e) Turner, D. R.; Paterson; M. J.; Steed, J. W. Chem. Commun. 2008, 1395-1397. f) Arunachalam, M.; Ravikumar, I.; Ghosh, P. J. Org. Chem. 2008,
, 9144-9147. g) Heyer, D.; Lehn J.-M. Tetrahedron Lett. 1986, 27, 5869-5872.
a) Mazik, M.; Sicking, W.; Boese, R. J. Org. Chem. 2004, 69, 7448-7462. b) Mazik, M.; Radunz, W.; Sicking, W. Org. Lett. 2002, 4, 4579-4582. c) Mazik, M. Chem. Soc. Rev. 2009, 38, 935-956.
a) Ilioundis, C. A.; Tocher, D. A.; Steed, J. W. J. Am. Chem. Soc. 2004, 126, 12395-12402. b) Okamoto, H.; Takemura, H.; Satake, K. Synthesis 2008, 39-44.
a) Pecoraro, V. L.; Weitl, F. L.; Raymond K. N. J. Am. Chem. Soc. 1981, 103, 5133-5140. b) Ebmeyer, F. Vögtle, F. Chem. Ber. 1989, 122, 1725-1727. c) Grammenudi, S.; Vögtle, F. Angew. Chem. Int. Ed. Engl. 1986, 98, 1119-1121. d) Lee, J. W.; Han, S. C., Kim J. H.; Lee, K. Bull. Korean Chem. Soc. 2006, 27, 1667-1670.
Nativi, C.; Cacciarini, M.; Francesconi, O.; Vacca, A.; Moneti, G.; Lenco, A. Roelens, S. J. Am. Chem. Soc. 2007, 129, 477-4385.
a) Usui, M.; Nishiwaki, T.; Anda, K.; Hida, M. Chem. Lett. 1984, 1561-1564. b) Bottino, F.;Grazia, M. D.; Finocchiaro, P.; FronSynthesis of Nitrogen-, Oxygen- and Sulphur-containing Tripodal Ligands with a Trimethylbenzene Core 175 czek, F. R.; Mamo, A.; Pappalardo, S. J. Org. Chem. 1988, 53, 3521-3529.
a) Gibson, F. S.; Bergmeier S. C.; Rapoport, H. J. Org. Chem.
, 59, 3216-3218. b) Varala, R.; Nuvula, S.; Adapa. S. R. J. Org. Chem. 2006, 71, 8283-8286.
Dietrich, B.; Hosseini, M. W.; Lehn, J.-M.; Sessions, R. B. Helv. Chim. Acta 1985, 68, 289-299.
Wallace, K. J.; Hanes, R.; Anslyn, E.;Morey, J.; Kilway, K. V.; Siegel, J. Synthesis 2005, 2080-2083.
Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897-3899.
a) Zard, S. Z. Angew. Chem. Int. Ed. Engl.1997, 36, 672-685. b) Quiclet-Sire, B.; Zard, S. Z. Chem. Eur. J. 2006, 12, 6002-6016. c) Degani, I.; Fochi, R. Synthesis, 1978, 365-368.
Bernard, J.; Favier, A.; Zhang, L.; Nilasaroya, A.; Davis, T. P.;
Barner-Kowollik, C.; Stenzel, M. H. Macromolecules 2005, 38, 5475-5484.
a) García-Merinos, J. P.; Hernández-Pérez, J. P.; Martínez-García, L.; Rojas-Lima, S.; López-Ruiz, H. J. Mex. Chem. Soc. 2007, 51, 209-212. b) Zard, Z. S. In: Radical Reactions in Organic Synthesis; Oxford Chemistry Masters: Oxford, 2003. c) Renaud, P.; Sibi,
M. P., in: Radicals in Organic Synthesis: Renaud, P., Sibi, M. P. Eds,: Wiley-VCH Weinheim, 2001. 2.
Still, W. C.; Kahn, M; Mitra, A.; J. Org. Chem. 1978, 43, 2923-2925.
Rehse, K.; Luekens, U.; Claus, G.; Archiv der Pharmazie 1987, 320, 1233-1238.
Wuytswinkel, G. V.; Verheyde, B.; Compernolle, F.; Toppet, S.; Dehaen, W. J. Chem. Soc., Perkin Trans. 1, 2000, 1337-1340. 20. Grawe, T.; Schrader, T.; Zadmard, R.; Kraft, A. J. Org. Chem. 2002, 67, 3755-3763.
Chiu, J. J.; Hart, H.; Ward, D. L. J. Org. Chem. 1993, 58, 964-966.
a) Bruker Analytical X-ray Systems. SMART: Bruker Molecular Analysis Research Tool, Versions 5.057 and 5.618, 1997 and 2000. b) Bruker Analytical X-ray Systems. SAINT NT, Versions 6.01 and 6.04, 1999 and 2001. c) Sheldrick, G. M. SHELX86, Program for Crystal Structure Solution; University of Göttingen: Germany, 1986. d) Bruker Analytical X-ray Systems. SHELXTLNT Versions 5.10 and 6.10, 1999 and 2000.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
