Ring-opening mechanism of lithium bromosilacyclopropylidenoids to silaallenes

Organometallics

Volumn 29, Issue 24, 2010, Pages 6739-6743

  Azizoglu, Akin ^a   Yildiz, Cem B ^b  

^a BALIKESIR UNIVERSITY   (Turkey)

^b AKSARAY UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO; HIGH-ENERGY BARRIERS; QUANTUM-MECHANICAL CALCULATION; RING OPENING; RING OPENING REACTION;

LITHIUM; QUANTUM THEORY;

DENSITY FUNCTIONAL THEORY;

EID: 78650670915     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100868b     Document Type: Article

References (49)

1. For reviews, see: Escudie, J.; Ranaivonjatovo, H.; Rigon, L. Chem. Rev. 2000, 100, 3639-3696
2. Eichler, B.; West, R. Adv. Organomet. Chem. 2001, 46, 1-46
3. Karni, M.; Apeloig, Y.; Kapp, J.; Schleyer, P.; von, R. In The Chemistry of Organic Silicon Compounds; Rappoport, Z.; Apeloig, Y., Eds.; John Wiley & Sons: Chichester, 2001; Vol. 3, pp 1 - 163.
4. Escudie, J.; Ranaivonjatovo, H. Organometallics 2007, 26, 1542-1559
5. Miracle, G. E.; Ball, J. L.; Powell, D. R.; West, R. J. Am. Chem. Soc. 1993, 115, 11598-11599
6. Trommer, M.; Miracle, G. E.; Eichler, B. E.; Powell, D. R.; West, R. Organometallics 1997, 16, 5737-5747
7. Spirk, S.; Belaj, F.; Albering, J. H.; Pietschning, R. Organometallics 2010, 29, 2981-2986
8. Bertrand, G.; Manuel, G.; Mazerolles, P. Tetrahedron 1978, 34, 1951-1956
9. Urbanová, M.; Volnina, E. A.; Gusel'nikov, L. E.; Bastl, Z.; Pola, J. J. Organomet. Chem. 1996, 509, 73-76
10. Goetze, B.; Herrschaft, B.; Auner, N. Chem. - Eur. J. 1997, 3, 948-957
11. De Meijere, A.; Faber, D.; Heinecke, U.; Walsh, R.; Muller, T.; Apeloig, Y. Eur. J. Org. Chem. 2001, 663-680
12. Mieusset, J. -L.; Brinker, U. H. J. Org. Chem. 2005, 70, 10572-10575
13. Satoh, T. Chem. Soc. Rev. 2007, 36, 1561-1572
14. Averina, E. B.; Sedenkova, K. N.; Borisov, I. S.; Grishin, Y. K.; Kuznetzova, T. S.; Zefirov, N. S. Tetrahedron 2009, 65, 5693-5701
15. Kilbas, B.; Azizoglu, A.; Balci, M. J. Org. Chem. 2009, 74, 7075-7083
16. Backes, J.; Brinker, U. H. In Houben-Weyl (Methoden der Organischen Chemie); Regitz, M., Ed.; Thieme: Stuttgart, Germany, 1989; Vol. E19b, pp 391 - 510.
17. Siegel, H. Top. Curr. Chem. 1982, 106, 55-78
18. Doering, W. v. E.; LaFlamme, P. M. Tetrahedron 1958, 2, 75-79
19. Moore, W. R.; Ward, H. R. J. Org. Chem. 1960, 25, 2073-2073
20. Moore, W. R.; Ward, H. R.; Merritt, R. F. J. Am. Chem. Soc. 1961, 83, 2019-2020
21. Skatteb̃l, L. Tetrahedron Lett. 1961, 5, 167-172
22. Some recent papers for the Doering-Moore-Skatteb̃l reaction: Alg̈, F.; Özen, R.; Balc̈, M. Tetrahedron Lett. 2002, 43, 3129-3131
23. Azizoglu, A.; Özen, R.; Hökelek, T.; Balci, M. J. Org. Chem. 2004, 69, 1202-1206
24. Christl, M.; Brauen, M.; Fischer, H.; Groetsch, S.; Müller, G.; Leusser, D.; Deurlein, S.; Stalke, D.; Arnone, M.; Engels, B. Eur. J. Org. Chem. 2006, 5045-5058
25. Azizoglu, A.; Demirkol, O.; Kilic, T.; Yildiz, Y. K. Tetrahedron 2007, 63, 2409-2413
26. Eccles, W.; Jasinski, M.; Kaszynski, P.; Zienkiewicz, K.; Stulgies, B.; Jankowiak, A. J. Org. Chem. 2008, 73, 5732-5744
27. Christl, M.; Fischer, H.; Arnone, M.; Engels, B. Chem. - Eur. J. 2009, 15, 11266-11272
28. Mahlokozera, T.; Goods, J. B.; Childs, A. M.; Thamattoor, D. M. Org. Lett. 2009, 11, 5095-5097
29. Sigal, N.; Apeloig, Y. J. Organomet. Chem. 2001, 636, 148-156
30. Azizoglu, A.; Balci, M.; Mieusset, J. -L.; Brinker, U. H. J. Org. Chem. 2008, 73, 8182-8188
31. Frisch, M. J.; et al. Gaussian 03, revision C.2; Gaussian, Inc.: Wallingford, CT, 2004. Full reference given in the Supporting Information.
32. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, U.K., 1989.
33. Fukui, K. J. Phys. Chem. 1970, 74, 4161-4162
34. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
35. IRC plots are available in the Supporting Information.
36. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
37. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1991, 95, 5853-5860
38. GaussView, Version 3.09; Dennington, R., II.; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. Semichem, Inc.: Shawnee Mission, KS, 2003.
39. Cramer, C. J.; Worthington, S. E. J. Phys. Chem. 1995, 99, 1462-1465
40. Kakkar, R.; Padhi, B. S. Int. J. Quantum Chem. 1996, 58, 389-398
41. Barthelat, J.-C.; Trinquier, G.; Bertrand, G. J. Am. Chem. Soc. 1979, 101, 3785-3789
42. Su, M.-D.; Amos, R. D.; Handy, N. C. J. Am. Chem. Soc. 1990, 112, 1499-1504
43. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096
44. Bettinger, H. F.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F. J. Phys. Chem. 1996, 100, 16147-16154
45. Sigal, N.; Apeloig, Y. Organometallics 2002, 21, 5486-5493
46. Gordon, M. S.; Koob, R. D. J. Am. Chem. Soc. 1981, 103, 2939-2944
47. Maier, G.; Peter, H.; Reisenauer, P.; Egenolf, H. Eur. J. Org. Chem. 1998, 1313-1317
48. Skancke, P. N.; Hrovat, D. A.; Borden, W. T. J. Phys. Chem. A 1999, 103, 4043-4048
49. Becerra, R.; Cannady, J. P.; Dormer, G.; Walsh, R. J. Phys. Chem. A 2008, 112, 8665-8677