Conformationally locked bridged bicyclic diselenides: Synthesis, structure, Se⋯O interaction, and theoretical studies

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5313-5319

  Sureshkumar, Devarajulu ^a   Ganesh, Venkataraman ^a   Chandrasekaran, Srinivasan ^a,b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DIHEDRAL ANGLES; DISELENIDES; NUCLEOPHILIC RING OPENING; PHYSICOCHEMICAL CHARACTERISTICS;

AMMONIUM COMPOUNDS; CONFORMATIONS; NUCLEOPHILES; REGIOSELECTIVITY; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

SELENIUM COMPOUNDS;

DISELENIDE DERIVATIVE; EPOXIDE; SELENIDE; TETRAETHYLAMMONIUM TETRASELENOTUNGSTATE; TETRYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS; THEORETICAL STUDY;

EID: 34447302023     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070705k     Document Type: Article

References (42)

1. (a) Barltrop, J. A.; Hayes, P. M.; Calvin, M. J. Am. Chem. Soc. 1954, 76, 4348-4367.
2. (b) Beecham, A. F.; Fridrichsons, J.; Mathieson, A. M. Tetrahedron Lett. 1966, 7, 3131-3138.
3. (c) Bergson, G.; Sjoberg, B.; Tweit, R. C.; Dodson, R. M. Acta Chem. Scand. 1960, 14, 222-223.
4. Wilson, R. M.; Buchanan, D. N.; Davis, J. N. Tetrahedron Lett. 1971, 12, 3919-3922.
5. (a) Folkins, P. L.; Harpp, D. N. J. Org. Chem. 1991, 56, 904-906.
6. (b) Folkins, P. L.; Harpp, D. N. J. Org. Chem. 1992, 57, 2013-2017.
7. Tonkikh, N.; Duddeck, H.; Petrova, M.; Neilands, O.; Strakovs, A. Eur. J. Org. Chem. 1999, 1585-1588.
8. (a) Saravanan, V.; Porhiel, E.; Chandrasekaran, S. Tetrahedron Lett. 2003, 44, 2257-2260.
9. (b) Bhat, R. G.; Porhiel, E.; Saravanan, V.; Chandrasekaran, S. Tetrahedron Lett. 2003, 44, 5251-5253.
10. (c) O'Neal, S.; Kollis, J. W. J. Am. Chem. Soc. 1998, 110, 1971-1973.
11. (d) Muller, A.; Diemann, E.; Jostes, R.; Bogge, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 934-955.
12. Sureshkumar, D.; Gunasundari, T.; Saravanan, V.; Chandrasekaran, S. Tetrahedron Lett. 2007, 48, 623-626.
13. There are no synthetic procedures reported in the literature for the synthesis of cis-1,4-bis-aziridines.
14. 3CN/EtOH; 1:1, 28°C) failed to give locked diselenides even under sonication conditions. This is due to a lack of reactivity of 1 towards epoxides.
15. (a) Brien, O. P.; Pilgram, C. D. Org. Biomol. Chem. 2003, 1, 523-534.
16. (b) Sureshkumar, D.; Maity, S.; Chandrasekaran, S. J. Org. Chem. 2006, 71, 1653-1657.
17. (a) Lin, P.; Bellos, K.; Stamm, H.; Onistschenko, A. Tetrahedron 1992, 48, 2359-2372.
18. (b) Tanner, D. Angew. Chem., Int. Ed. 1994, 33, 599-619.
19. (c) Stamm, H. J. Prakt. Chem. 1999, 341, 319-331.
20. (d) Davis, F. A.; Coull, S. M. Synthesis 2000, 1347-1365.
21. (e) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
22. (f) Sureshkumar, D.; Koutha, S.; Chandrasekaran, S. J. Am. Chem. Soc. 2005, 127, 12760-12761.
23. (g) Li, P.; Forbeck, E. M.; Evans, C. D.; Joullie, M. M. Org. Lett. 2006, 8, 5105-5107.
24. Chao, B.; Dittmer, D. C. Tetrahedron Lett. 2001, 42, 5789-5791.
25. CCDC 292058 (3), CCDC 610604 (12), CCDC 610605 (13), CCDC 610606 (14), CCDC 610607 (16), CCDC 610608 (18), CCDC 610609 (19), CCDC 610610 (20), CCDC 610611 (21), CCDC 610612 (24), and CCDC 292060 (26) contain supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallography Data Centre via www.ccdc.cam.ac.uk/ datarequest/cif.
26. (a) Kruhlak, N. L.; Wang, M.; Boorman, P. M.; Parvez, M. Inorg. Chem. 2001, 40, 3141-3148.
27. (b) Boorman, P. M.; Wang, M.; Parvez, M. J. Chem. Soc., Chem. Commun. 1995, 999-1000.
28. (c) Gea, Y.; Greaney, M. A.; Coyle, C. L.; Stiefel, E. I. J. Chem. Soc., Chem. Commun. 1992, 160-161 and references cited therein.
29. 2 was identified as one of the major inorganic byproducts after reaction.
30. (a) B3LYP is Becke's three parameter hybrid method using the LYP correlation functional. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
32. (c) Vosoko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
33. Calculations were performed using the Gaussian 98 program. For further reference, see the Supporting Information.
34. Pearson, J. K.; Ban, F.; Boyd, R. J. J. Phys. Chem. A 2005, 109, 10373-10379 and references cited therein.
35. Pearson, J. K.; Boyd, R. J. J. Phys. Chem. A 2006, 110, 8979-8985.
36. (a) Iwaoka, M.; Komatsu, H.; Katsuda, T.; Tomoda, S. J. Am. Chem. Soc. 2004, 126, 5309-5317.
37. (b) Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477-11485.
38. (a) Bates, G. S.; Varelas, M. A. Can. J. Chem. 1980, 58, 2562-2566.
39. (b) Lohray, B. B.; Gao, Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623-2626.
40. (c) Berry, M. B.; Craig, D. Synlett 1992, 41-44.
41. (d) Bieber, L. W.; De Araujo, M. C. F. Molecules 2002, 7, 902-906.
42. Sureshkumar, D.; Maity, S.; Chandrasekaran, S. Tetrahedron 2006, 62, 10162-10170.