Iminophosphorane-based synthesis of multinuclear ferrocenyl urea, thiourea and guanidine derivatives and exploration of their anion sensing properties

Tetrahedron

Volumn 65, Issue 7, 2009, Pages 1397-1401

  Lorenzo, Ángeles ^a   Aller, Enrique ^a   Molina, Pedro ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

Anion sensing; Aza Wittig reaction; Electrochemistry; Iminophosphoranes

Indexed keywords

ANION; AZIDE; CARBON DIOXIDE; CARBON DISULFIDE; FERROCENE DERIVATIVE; GUANIDINE DERIVATIVE; PHOSPHATE; PHOSPHORANE DERIVATIVE; THIOUREA DERIVATIVE; UREA DERIVATIVE;

ARTICLE; ELECTROCHEMISTRY; OXIDATION REDUCTION POTENTIAL; POLAROGRAPHY; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; WITTIG REACTION;

EID: 58149343251     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.030     Document Type: Article

References (67)

1. For reviews, see:
2. Molina P., and Vilaplana M.J. Synthesis (1994) 1197-1218
3. Fresneda P.M., and Molina P. Synlett (2004) 1-17
4. Arques A., and Molina P. Curr. Org. Chem. 8 (2004) 827-843
5. Molina P., Tarraga A., Curiel D., and Ramirez de Arellano C. Tetrahedron 55 (1999) 1417-1426
6. Tarraga A., Molina P., Lopez J.L., Velasco M.D., Bautista D., and Jones P.G. Organometallics 21 (2002) 2055-2065
7. Tarraga A., Molina P., Curiel, and Velasco M.D. Organometallics 20 (2001) 2145-2152
8. Tarraga A., Molina P., Curiel D., and Velasco M.D. Tetrahedron 57 (2001) 6765-6774
9. Molina P., Tarraga A., and Curiel D. Synlett (2002) 435-438
10. Caballero A., Lloveras V., Curiel D., Tarraga A., Espinosa A., Garcia R., Vidal-Gancedo J., Rovira C., Wurst K., Molina P., and Veciana J. Inorg. Chem. 46 (2007) 825-838
11. Tarraga A., Otón F., Espinosa A., Velasco M.D., Molina P., and Evans D.J. Chem. Commun. (2004) 458-459
12. Molina P., Tarraga A., and Caballero A. Eur. J. Inorg. Chem. (2008) 3401-3417
13. Fan E., Van Arman S.A., Kincaid S., and Hamilton A.D. J. Am. Chem. Soc. 115 (1993) 369-370
14. Hamann B.C., Branda N.R., and Rebek Jr. J. Tetrahedron Lett. 34 (1993) 7837-7840
15. Noshizawa S., Bühlmann P., Iwao M., and Umezawa Y. Tetrahedron Lett. 36 (1995) 6483-6486
16. Werner F., and Schneider H.-J. Helv. Chim. Acta 83 (2000) 465-478
17. Lee C., Lee D.H., and Hong J.-I. Tetrahedron Lett. 42 (2001) 8665-8668
18. Ayling A.J., Perez-Payan M.N., and Davis A.P. J. Am. Chem. Soc. 123 (2001) 12716-12717
19. Budka J., Lhotak P., Michlova V., and Stibor I. Tetrahedron Lett. 42 (2001) 1583-1586
20. Hoffman R.W., Hettche F., and Harms K. Chem. Commun. (2002) 782-783
21. Hettche F., Reiss P., and Hoffman R.W. Chem.-Eur. J. 8 (2002) 4946-4956
22. Sisson A.L., Clare J.P., Taylor L.H., Charmant J.P.H., and Davis A.P. Chem. Commun. (2003) 2246-2247
23. Dudic M., Lhotak P., Stibor I., Lang K., and Proskova P. Org. Lett. 5 (2003) 149-152
24. Bondy C.R., Gale P.A., and Loeb S.J. J. Am. Chem. Soc. 126 (2004) 5030-5031
25. Lee L.Y., Cho E.J., Mukamel S., and Nam K.C. J. Org. Chem. 69 (2004) 943-950
26. Kwon J.Y., Jang Y.J., Kim S.K., Lee K.-H., Kim J.S., and Yoon J. J. Org. Chem. 69 (2004) 5155-5157
27. Turner D.R., Spencer E.C., Howard J.A.K., Tocher D.A., and Steed J.W. Chem. Commun. (2004) 1352-1353
28. Jose D.A., Kumar D.K., Ganguly B., and Das A. Tetrahedron Lett. 46 (2005) 5343-5346
29. Esteban-Gomez D., Fabbrizzi L., and Licchelli M. J. Org. Chem. 70 (2005) 5717-5720
30. Boiocchi M., Del Boca L., Esteban-Gomez D., Fabbrizzini L., Licchelli M., and Monzani E. Chem.-Eur. J. 11 (2005) 3097-3104
31. Hay B.P., Firman T.K., and Moyer B.A. J. Am. Chem. Soc. 127 (2005) 1810-1819
32. Bryantsev V.S., and Hay B.P. J. Mol. Chem.: TEOCHEM 725 (2005) 177-182
33. Pratt M.D., and Beer P.D. Polyhedron 22 (2003) 649-653
34. Alonso B., Casado C.M., Cuadrado I., Moran M., and Kaifer A.E. Chem. Commun. (2002) 1778-1779
35. Miyaji H., Collinson S.R., Prokes I., and Tucker J.H.R. Chem. Commun. (2003) 64-65
36. Otón F., Tarraga A., Velasco M.D., Espinosa A., and Molina P. Chem. Commun. (2004) 1658-1659
37. Otón F., Tárraga A., Espinosa A., Velasco M.D., Bautista D., and Molina P. J. Org. Chem. 70 (2005) 6603-6608
38. Otón F., Tarraga A., Espinosa A., Velasco M.D., and Molina P. J. Org. Chem. 71 (2006) 4590-4598
39. Willener Y., Joly K.M., Moody C.J., and Tucker J.H.R. J. Org. Chem. 73 (2008) 1225-1233
40. Gale P.A. Coord. Chem. Rev. 240 (2003) 1-226
41. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609-1646
42. Sessler J.L., Gale P.A., and Cho W.-S. Anion Receptor Chemistry (2006), RSC, Cambridge pp 193-202
43. Gunlaugsson T., Glynn M., Tocci G.M., Kruger P.E., and Pfeffer F.M. Coord. Chem. Rev. 250 (2006) 3094-3117
44. Beer P.D., Cavis J.J., Drillma-Milgrom A., and Szemes F. Chem. Commun. (2002) 1716-1717
45. Hannon C.L., and Anslyn E.V. In: Duggas H., and Schmidtchen F.P. (Eds). Biorganic Chemistry Frontiers Vol. 3 (1993), Springer, Berlin 193-255
46. Best M.D., Tobey S.L., and Anslyn E.V. Coord. Chem. Rev. 240 (2003) 3-15
47. Baily P.J., and Pace S. Coord. Chem. Rev. 214 (2001) 91-141
48. Coles M.P. Dalton Trans. (2006) 985-1001
49. Aioki S., Iwaida K., Hanamoto N., Shiro M., and Kimura E. J. Am. Chem. Soc. 124 (2002) 5256-5257
50. For a review, see:
51. Beer P.D., Gale P.A., and Chen Z. Coord. Chem. Rev. 185-186 (1999) 3-36
52. For recent examples, see:
53. Caballero A., Lloveras V., Tárraga A., Espinosa A., Velasco M.D., Vidal-Gancedo J., Rovira C., Wurst K., Molina P., and Veciana L. Angew. Chem., Int. Ed. 44 (2005) 1977-1981
54. Caballero A., Martinez R., Lloveras V., Ratera I., Vidal-Gancedo J., Wurst K., Tárraga A., Molina P., and Veciana J. J. Am. Chem. Soc. 127 (2005) 15666-15667
55. Zapata F., Caballero A., Espinosa A., Tarraga A., and Molina P. Org. Lett. 9 (2007) 2385-2388
56. For reviews, see:
57. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486-516
58. Gale P.A. Coord. Chem. Rev. 199 (2000) 181-233
59. Gale P.A. Coord. Chem. Rev. 213 (2001) 79-128
60. For a recent example, see:
61. Zapata F., Caballero A., Espinosa A., Tarraga A., and Molina P. J. Org. Chem. 73 (2008) 4034-4044
62. Westwood J., Coles S.J., Collison S.R., Gasser G., Green S.J., Hursthouse M.B., Light M.E., and Tucker J.H.R. Organometallics 23 (2004) 946-951 and references therein
63. Beer P.D., Drew M.G.B., and Smith D.K. J. Organomet. Chem. 543 (1997) 259-261
64. Otón F., Tarraga A., and Molina P. Org. Lett. 8 (2006) 2107-2110
65. Otón F., Espinosa A., Tarraga A., Ramirez de Arellano C., and Molina P. Chem.-Eur. J. 13 (2007) 5742-5752
66. Bublitz D.E. J. Organomet. Chem. 23 (1970) 225-228
67. Molina P., Aller E., and Lorenzo A. Synlett (2003) 714-716