Synthesis of azolyl carboximidamides as ligands for Zn(II) and Cu(II): Application of the Zn(II) complexes as catalysts for the copolymerization of carbon dioxide and epoxides

Journal of Organic Chemistry

Volumn 71, Issue 4, 2006, Pages 1399-1406

  Walther, Martin ^a   Wermann, Kurt ^b   Lutsche, Marion ^b   Günther, Wolfgang ^b   Görls, Helmar ^b   Anders, Ernst ^b  

^a INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZOLYL CARBOXIMIDAMIDES; EPOXIDES; METAL COMPLEXES; TRIAZINIUM SALTS;

CARBON DIOXIDE; COMPLEXATION; COPOLYMERIZATION; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

NITROGEN COMPOUNDS;

AMIDE; AMINE; CARBON DIOXIDE; COPPER COMPLEX; CYCLOHEXENE DERIVATIVE; EPOXIDE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; LIGAND; METAL COMPLEX; POLYCARBONATE; POLYETHER DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; ZINC COMPLEX;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; CRYSTAL STRUCTURE; MOLECULAR WEIGHT; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; CARBON DIOXIDE; CARBONATES; CATALYSIS; COPPER; EPOXY COMPOUNDS; IMIDAZOLES; LIGANDS; POLYMERS; PYRIDINES; ZINC;

EID: 33644550937     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052056n     Document Type: Article

References (60)

1. Bis-(1,2,4-thiadiazolo)-1,3,5-triazinium halides. 9. For part 8, see: Wermann, K.; Walther, M.; Günther, W.; Görls, H.; Anders, E. Tetrahedron 2005, 61, 673-685.
2. (a) Berlinck, R. G. S. Nat. Prod. Rep. 2002, 19, 617-649.
3. (b) Berlinck, R. G. S. Nat. Prod. Rep. 1999, 16, 339-409.
4. (a) The Pharmacological Basis of Therapeutics, 7th ed.; Gilman, A. G., Goodman, L. S., Rall, T. W., Murad, F., Eds.; Pergamon Press: New York, 1990; p 899.
5. (b) Hu, L. Y.; Guo, J.; Magar, S. S.; Fischer, J. B.; Burke-Howie, K. J.; Durant, G. J. J. Med. Chem. 1997, 40, 4281-4289.
6. (a) Ishikawa, T.; Isobe, T. Chem.-Eur. J. 2002, 8, 552-557.
7. (b) Isobe, T.; Fukuda, K.; Araki, Y.; Ishikawa, T. Chem. Commun. 2001, 243-244.
8. Costa, M.; Chiusoli, G. P.; Taffurelli, D.; Dalmonego, G. J. Chem. Soc., Perkin Trans. 1 1998, 1541-1546.
9. See ref 13e and literature cited therein.
10. (a) Manimala, J.; Anslyn, E. V. Eur. J. Org. Chem. 2002, 3909-3922.
11. (b) Zapf, C. W.; Creighton, C. J.; Tomioka, M.; Goodman, M. Org. Lett. 2001, 3, 1133-1136.
12. (c) Guisado, O.; Martinez, S.; Pator, J. Tetrahedron Lett. 2002, 43, 7105-7109.
13. (a) Wittmann, H.; Raab, V.; Schorn, A.; Plackmeyer, J.; Sundermeyer, J. Eur. J. Inorg. Chem. 2001, 1937-1948.
14. (b) Wittmann, H.; Schorn, A.; Sundermeyer, J. Z. Anorg. Chem. 2000, 625, 1583-1590.
15. (c) Muche, M. S.; Göbel, M. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2126-2129.
16. (d) Deslongchamps, G.; Galan, A.; de Mendoza, J.; Rebek, J., Jr, Angew. Chem., Int. Ed. Engl. 1992, 31, 61-63.
17. Aoki, S.; Iweida, K.; Hanamoto, N.; Shiro, M.; Kimura, E. J. Am. Chem. Soc. 2002, 124, 5256-5257.
18. Coles, M. P.; Hitchcock, P. B. Eur. J. Inorg. Chem. 2004, 2662-2672.
19. Coates, G. W.; Moore, D. R. Angew. Chem. 2004, 116, 6784-6806.
20. (a) Siedle, A. R.; Webb, J. R.; Behr, F. E.; Newmark, R. A.; Weil, D. A.; Erickson, K.; Naujok, R.; Brostrom, M.; Mueller, M.; Chou, S.-H.; Young, V. G., Jr. Inorg. Chem. 2003, 42, 932-934.
21. (b) Dias, H. V. R.; Singh, S. Inorg. Chem. 2004, 43, 5786-5788.
22. (c) Dias, H. V. R.; Singh, S. Inorg. Chem. 2004, 43, 7396-7402.
23. (a) Wermann, K.; Walther, M.; Günther, W.; Görls, H.; Anders, E. J. Org. Chem. 2001, 66, 720-726.
24. (b) Walther, M.; Wermann, K.; Görls, H.; Anders, E. Synthesis 2001, 1327-1330.
25. (c) Wermann, K.; Walther, M.; Anders, E. ARKIVOC (Gainesville, FL) 2002, 10, 24-33.
26. (d) Wermann, K.; Walther, M.; Görls, H.; Anders, E. Synlett 2003, 1459-1462.
27. (e) Wermann, K.; Walther, M.; Günther, W.; Görls, H.; Anders, E. Eur. J. Org. Chem. 2003, 1389-1403.
28. (a) Anders, E.; Vanden Eynde, J.-J.; Wermann, K. Adv. Heterocycl. Chem. 2000, 77, 18.3-219.
29. (b) Anders, E.; Opitz, A.; Wermann, K.; Wiedel, B.; Walther, M.; Imhof, W.; Görls, H. J. Org. Chem. 1999, 64, 3113-3121.
30. Anders, E.; Wermann, K.; Wiedel, B.; Günther, W.; Görls, H. Eur. Org. Chem. 1998, 2923-2930.
31. Scott, D. A.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1484-1485, and literature cited therein.
32. Matti, J.; Ledoux, C.; Kesler, E. Bull. Soc. Chim. Fr. 1959, 477-479.
33. Van der Plas, H. C. In Adv. in Heterocycl. Chem.: Degenerate Transformations of Heterocyclic Compounds: Katritzky, A. R., Ed.; Academic Press: New York, 1999; p 87.
34. C4a = +0.30 e B3LYP/6-311++D(d,p) opt.
35. Nilsson Lill, S. O.; Rauhut, G.; Anders, E. Chem. Eur. J. 2003, 9, 3143-3153.
36. Michelsen, K. Acta Chem. Scand. 1974, A28, 428-434.
37. Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018-11019.
38. Abu-El-Wafa, S. M.; El-Ries, M. A.; Ahmed, F. A. Inorg. Chim. Acta 1987, 136, 127-131.
39. Pickardt, J.; Kühn, B. Z. Naturforsch., B 1996, 51, 1494-1472.
40. (a) DFT-calculations were performed using the GAUSSIAN 98 suite of programs, revision A.11: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A. J.; Cheeseman, R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98, revision A.11; Gaussian Inc.: Pittsburgh, PA, 1998.
41. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
42. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785-789.
43. Kunert, M.; Bräuer, M.; Klobes, O.; Görls, H.; Dinjus, E.; Anders, E. Eur. J. Inorg. Chem. 2000, 1803-1809.
44. Darensbourg, D. J.; Holtcamp, M. W.; Struck, G. E.; Zimmer, M. S.; Niezgoda, S. A.; Rainey, P.; Robertson, J. B.; Draper, J. D.; Reibenspies, J. H. J. Am. Chem. Soc. 1999, 121, 107-116.
45. + complexes (R = aryl, alky) appears to be justified but has to be quantified by further theoretical investigation.
46. Ruben, M.; Walther, D.; Knake, R.; Görls, H.; Beckert, R. Eur. Inorg. Chem. 2000, 1055-1060.
47. Arakawa, H.; Aresta, M.; Armor, J. M.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; DuBois, D. E.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. E.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer, L. E.; Marks, T. J.; Morokuma, K.; Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953-996.
48. (a) Inoue, S.; Koinuma, H.; Tsuruta, T. J. Polym. Sci., Part B: Polym. Lett. 1969, 7, 287-292.
49. (b) Soga, K.; Uenishi, K.; Hosoda, S. W. J. Polym. Sci., Part B: Polym. Lett. 1985, 23, 299-304.
50. (c) Kuran, W.; Listos, T. Macromol. Chem. 1994, 19, 977-984.
51. Darensbourg, D. J.; Rainey, P.; Yarbrough, J. Inorg. Chem. 2001, 40, 986-993.
52. (a) Coates, G. W. J. Chem. Soc., Dalton Trans. 2002, 467-475.
53. (b) Cheng, M.; Darling, N. A.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2000, 2007-2008.
54. Taveras, A. G.; Doll, R. J.; Cooper, A. B.; Ferreira, J. A.; Guzi, T.; Rane, D. F.; Girijavallabhan, V. M.; Aki, C. J.; Chao, J.; Alvarez, C.; Kelly, J. M.; Lalwani, T.; Desai, J. A.; Wang, J. J-s. (Schering Corp., USA) U.S. 6372747, 2002; Chem. Abstr. 2002, 136, 309918.
55. MOLEN, An Interactive Structure Solution Procedure; Enraf-Nonius: Delft, Netherlands, 1990.
56. COLLECT, Data Collection Software; Nonius B. V.: Delft, Netherlands, 1998.
57. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Carter, C. W., Sweet, R. M., Eds.; Macromolecular Crystallography, Part A; Academic Press: San Diego, CA, 1997; Vol. 276, pp 307-326.
58. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-473.
59. Sheldrick, G. M. SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.
60. CCDC 282561 (Cu-4d) and 282562 (4f/2) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, United Kingdom; fax: (+44) 1223-336-033: or deposit@ccdc.cam.ac.uk).