Synthesis of sterically encumbered organoselenium species and their selectivity towards Hg(II) ions

Tetrahedron Letters

Volumn 48, Issue 27, 2007, Pages 4737-4741

  Maheshwari, Monika ^a   Khan, Shabana ^a   Singh, Jai Deo ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Hg2+ ions; Host guest systems; Ion selective electrodes; Tetraalkyl selenium

Indexed keywords

IONOPHORE; MERCURY; ORGANOSELENIUM DERIVATIVE; SELENIUM;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ELECTRODE; GEOMETRY; SYNTHESIS;

EID: 34249900482     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.020     Document Type: Article

References (32)

1. Milton M.D., Singh J.D., and Butcher R.J. Tetrahedron Lett. 45 (2004) 6745-6747
2. Milton M.D., Kumar N., Sokhi S.S., Singh S., Maheshwari M., Singh J.D., Asnani M., and Butcher R.J. Tetrahedron Lett. 45 (2004) 8941-8944
3. Milton M.D., Khan S., Singh J.D., Mishra V., and Khandelwal B.L. Tetrahedron Lett. 46 (2005) 755-758
4. Kumar N., Milton M.D., Singh J.D., Upreti S., and Butcher R.J. Tetrahedron Lett. 47 (2006) 885-889
5. Werz D.B., Gleiter R., and Rominger F. J. Am. Chem. Soc. 124 (2002) 10638-10639
6. Werz D.B., and Gleiter R. J. Org. Chem. 68 (2003) 9400-9405
7. Bleiholder C., Gleiter R., Werz D.B., and Köppel H. Inorg. Chem. 46 (2007) 2249-2260
8. Unpublished results from our laboratory: Kumar, N. Ph.D. Dissertation, Indian Institute of Technology, Delhi, India, 2005.
9. Singh, S. Ph.D. Dissertation, Indian Institute of Technology, Delhi, India, 2007.
10. For C-H⋯Se interactions see. Iwaoka M., and Tomoda S. J. Am. Chem. Soc. 116 (1994) 4463-4464
11. Michalczyk R., Schimdt J.G., Moody E., Li Z., Wu R., Dunlop R.B., Odom J.D., and 'Pete' Silks III L.A. Angew. Chem., Int. Ed. 39 (2000) 3067-3070
12. Zade S.S., Panda S., Singh H.B., Sunoj R.B., and Butcher R.J. J. Org. Chem. 70 (2005) 3693-3704
13. Werz D.B., Gleiter R., and Rominger F. J. Org. Chem. 69 (2004) 2945-2952
14. Bleiholder C., Werz D.B., Köppel H., and Gleiter R. J. Am. Chem. Soc. 128 (2006) 2666-2674
15. Mansfield N.E., Grundy J., Coles M.P., Avent A.G., and Hitchcock P.B. J. Am. Chem. Soc. 128 (2006) 13879-13893
16. Procedures similar to those used for arylseleno substitution were adopted and found to be equally effective and a successful strategy for alkylselenium substitution. For example, sodium alkylselenolate ions can be generated in situ by reduction of the corresponding dialkyl diselenide in aqueous THF with sodium borohydride at 0 °C. Alkylselenolate anions thus generated reacted cleanly with tetrabromomethylbenzene and, after completion of the reaction, the product in solution was recovered by conventional aqueous workup in excellent yields (>60%) and high purity. Milton M.D., Kumar N., Sokhi S.S., Singh S., and Singh J.D. Tetrahedron Lett. 45 (2004) 6453-6455
17. Kumar N., Milton M.D., and Singh J.D. Tetrahedron Lett. 45 (2004) 6611-6613
18. 4: C, 46.30; H, 6.87. Found: C, 45.46; H, 6.71.
19. Hope E.G., and Levason W. Coord. Chem. Rev. 122 (1993) 109-170
20. Levason W., and Reid G. J. Chem. Soc., Dalton Trans. (2001) 2953-2960
21. Levason W., Orchard S.D., and Reid G. Coord. Chem. Rev. 225 (2002) 159-199
22. Vögtle F., and Weber E. Angew. Chem., Int. Ed. Engl. 13 (1974) 814-816
23. 3, Z = 2, 14,662 reflections collected, 4747 [R(int) = 0.0593] independent reflections. Final R1 = 0.0782, and wR2 = 0.1652 (all data). This configuration allows the selenium atoms of the ligand to act as a bridging bidentate chelating ligand to coordinate with two mercury atoms providing a distorted tetrahedral arrangement around each mercury atom. Crystallographic data for the Hg(II) complex have been deposited at the Cambridge Crystallographic Data Centre, CCDC No. 602915. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (+44 1223 336408; e-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk).
24. 2.
25. 2+ and the sulfur atom. Bühlmann P., Pretsch E., and Bakker E. Chem. Rev. 98 (1998) 1593-1687
26. Ono A., and Togashi H. Angew. Chem., Int. Ed. 43 (2004) 4300-4302
27. Goldcamp M.J., Ashley K., Edison S.E., Pretty J., and Shumaker J. Electroanalysis 17 (2005) 1015-1018
28. Ros-Lis J.V., Marcos M.D., Máñez R.-M., Rurack K., and Soto J. Angew. Chem., Int. Ed. 44 (2005) 4405-4407
29. Anslyn E.V. J. Org. Chem. 72 (2007) 687-699
30. Wakabayashi S., Kato Y., Mochizuki K., Suzuki R., Matsumoto M., Sugihara Y., and Shimizu M. J. Org. Chem. 72 (2007) 744-749
31. 2+ ions with respect to their thio-analogues. Kumagai T., and Akabori S. Chem. Lett. (1989) 1667-1670
32. 2 and their transition metal complexes with Pd(II), Pt(II), Rh(III), Ru(II), Cu(I) and Ag(I) to explore the coordinating properties of the xylyl ligands in different coordination geometries and ligand binding modes. Levason W., Nirwan M., Ratnani R., Reid G., Tsoureas N., and Webster M. Dalton Trans. (2007) 439-448