Synthesis and conformational properties of substituted 1,4,2- oxazasilinanes: Low temperature NMR study and quantum chemical calculations

Tetrahedron

Volumn 68, Issue 4, 2012, Pages 1097-1104

  Lazareva, Nataliya F ^a   Albanov, Alexandr I ^a   Shainyan, Bagrat A ^a   Kleinpeter, Erich ^b  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

1,4,2 Oxazasilinanes; Conformational analysis; Dynamic NMR; Quantum chemical calculations; X ray analysis

Indexed keywords

1,4,2 OXAZASILINANE; METHYL IODIDE; ORGANOSILICON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; ROOM TEMPERATURE; X RAY ANALYSIS;

EID: 84855465303     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.077     Document Type: Article

References (56)

1. A.R. Bassindale, and P.G. Taylor Y.Z. Rappoport, The Chemistry of Organic Silicon Compounds Vol. 1 1989 John Wiley Chichester, UK-New York, NY-Brisbane-Toronto-Singapore 893
2. A.R. Bassindale, S.J. Glynn, and P.G. Taylor Z. Rappoport, Y. Apeloig, The Chemistry of Organic Silicon Compounds Vol. 2 1998 John Wiley Chichester, UK-New York, NY-Weinheim-Brisbane-Singapore-Toronto 355
3. J.R. Hwu, and N. Wang Chem. Rev. 89 1989 1599
4. J.M. White Aust. J. Chem. 48 1995 1227
5. J. Hermanns, and B. Schmidt J. Chem. Soc., Perkin Trans. 1 1998 2209
6. J. Hermanns, and B. Schmid J. Chem. Soc., Perkin Trans. 1 1999 81
7. G. Rousseau, and L. Blanco Tetrahedron 62 2006 7951
8. K.C. Majumdar, P.K. Basuy, and S.K. Chattopadhyay Tetrahedron 63 2007 793
9. Q. Shen, S. Rhodes, and J.C. Cochran Organometallics 11 1992 485
10. Y.L. Kuan, and J.M. White J. Chem. Soc., Chem. Commun. 1994 1195
11. R.R. Núñez, J. Unwalla, F.K. Cartledge, S.G. Cho, B.H. Riches, M.P. Glenn, N.L. Hungerford, L.K. Lambert, D.J. Brecknell, and W. Kitching J. Chem. Soc., Perkin Trans. 2 1997 1365
12. C.H. Marzabadi, J.E. Anderson, J. Gonzalez-Outeirino, P.R.J. Gaffney, C.G.H. White, D.A. Tocher, and L.J. Todaro J. Am. Chem. Soc. 125 2003 15163
13. A.J. Green, J. Giordano, and J.M. White Aust. J. Chem. 53 2000 285
14. C. Zheng, S. Subramaniam, V.F. Kalasinsky, and J.R. Durig J. Mol. Struct. 785 2006 143
15. D. Casarini, L. Lunazzi, and A. Mazzanti Tetrahedron 54 1998 13181
16. I. Arnason, G.K. Thorarinsson, and E. Matern Z. Anorg. Allg. Chem. 626 2000 853
17. I. Arnason, A. Kvaran, S. Jonsdottir, P.I. Gudnason, and H. Oberhammer J. Org. Chem. 67 2002 3827
18. S. Dez-Gonzalez, and L. Blanco J. Organomet. Chem. 691 2006 5531
19. L.B. Favero, B. Velino, W. Caminati, I. Arnason, and A. Kvaran J. Phys. Chem. A 110 2006 9995
20. L.B. Favero, B. Velino, W. Caminati, I. Arnason, and A. Kvaran Organometallics 25 2006 3813
21. A.J. Weldon, and G.S. Tschumper Int. J. Quantum Chem. 107 2007 2261
22. G.V. Girichev, N.I. Giricheva, A. Bodi, P.I. Gudnason, S. Jonsdottir, A. Kvaran, I. Arnason, and H. Oberhammer Chem. - Eur. J. 13 2007 1776
23. A. Bodi, A. Kvaran, S. Jonsdottir, E. Antonsson, S.Ó. Wallevik, I. Arnason, A.V. Belyakov, A.A. Baskakov, M. Hölbling, and H. Oberhammer Organometallics 26 2007 6544
24. P.I. Gudnason, and I. Arnason Org. Lett. 11 2009 2015
25. R. Bjornssona, and I. Arnason Phys. Chem. Chem. Phys. 11 2009 8689
26. S.Ó. Wallevik, R. Bjornsson, A. Kvaran, S. Jonsdottir, G.V. Girichev, N.I. Giricheva, K. Hassler, and I. Arnason J. Mol. Struct. 978 2010 209
27. S.O. Wallevik, R. Bjornsson, A. Kvaran, S. Jonsdottir, I. Arnason, A.V. Belyakov, A.A. Baskakov, K. Hassler, and H. Oberhammer J. Phys. Chem. A 114 2010 2127
28. R.J. Fessenden, and M.D. Coon J. Org. Chem. 29 1964 1607
29. M.J.O. Anteunis, and R. Dedeyne Org. Magn. Reson. 9 1977 127
30. S.V. Kirpichenko, A.T. Abrosimova, A.I. Albanov, and M.G. Voronkov Russ. J. Gen. Chem. 71 2001 1874
31. S.V. Kirpichenko, A.I. Albanov, and V.A. Pestunovich J. Sulfur Chem. 25 2004 21
32. C. Blaszykowski, C. Brancour, A.-L. Dhimane, L. Fensterbank, and M. Malacria Eur. J. Org. Chem. 2009 1674
33. S.V. Kirpichenko, E. Kleinpeter, and B.A. Shainyan J. Phys. Org. Chem. 23 2010 859
34. N.F. Lazareva, E.I. Brodskaya, and G.V. Ratovski J. Chem. Soc., Perkin Trans. 2 2002 2083
35. N.F. Lazareva, T.I. Vakul'skaya, A.I. Albanov, and V.A. Pestunovich Appl. Organomet. Chem. 20 2006 696
36. N.F. Lazareva, T.I. Vakul'skaya, and I.M. Lazarev J. Phys. Org. Chem. 22 2009 144
37. W. Simmler, W. Meise, and H. Walz Z. Anorg. Allg. Chem. 314 1962 245
38. W. Simmler Chem. Ber. 96 1963 349
39. A.A. Zhdanov, V.V. Pakhomov, and I.A. Arkhipov Izv. Akad. Nauk SSSR, Ser. Khim. 1967 1768
40. A.A. Zhdanov, V.V. Pakhomov, and I.A. Arkhipov Izv. Akad. Nauk SSSR, Ser. Khim. 1970 392
41. G.I. Orlov, A.A. Enukashvili, and V.M. D'yakov Zh. Obshch. Khim. 56 1986 2165
42. V.D. Sheludyakov, N.I. Kirilina, E.L. Kotrikadze, A.D. Kirilin, and E.A. Chernyshev Zh. Obshch. Khim. 52 1982 2646
43. V.D. Sheludyakov, E.L. Kotrikadze, and A.D. Kirilin Zh. Obshch. Khim. 54 1984 1134
44. Y.I. Baukov, A.G. Shipov, E.P. Kramarova, E.A. Mamaeva, O.A. Zamyshlyaeva, N.A. Anisimova, and V.V. Negrebetskii Russ. J. Org. Chem. 32 1996 1216
45. W. Naegele, A. De Montigny, and W. Simmler Z. Naturforsch. 25b 1970 11
46. I. Alkorta, and J. Elguero Magn. Reson. Chem. 42 2004 955
47. C.B. LeMaster, C.L. LeMaster, M. Tafazzoli, C. Suarez, and N.S. True J. Phys. Chem. 94 1990 3461
48. N.F. Lazareva, B.A. Shainyan, and E. Kleinpeter J. Phys. Org. Chem. 23 2010 84
49. L. Lunazzi, D. Casarini, M.A. Cremonini, and J.E. Anderson Tetrahedron 47 1991 7465
50. A.M. Belostotskii, P. Aped, and A. Hassner J. Mol. Struct. THEOCHEM 398-399 1997 427
51. A.J. Gordon, and R.A. Ford The Chemist's Companion 1972 John Wiley Chichester, UK
52. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution, Göttingen, 1997
53. C.B. Hübschle, G.M. Sheldrick, and B. Dittrich J. Appl. Cryst. 44 2011 1281
54. Sheldrick, G. M. SHELXS-04, Program for Crystal Structure Refinement, Göttingen, 2004
55. G.M. Sheldrick Acta Cryst. A64 2008 1285
56. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision B.03 2003 Gaussian Pittsburg, PA, CT