Synthesis, structural studies and desilylation reactions of some N-2-(trimethylsilyl)ethyl-N-nitrosocarbamates

Tetrahedron

Volumn 61, Issue 21, 2005, Pages 4939-4948

  Thakkalapally, Arpitha ^a   Benin, Vladimir ^a  

^a UNIVERSITY OF DAYTON   (United States)

Author keywords

2 (Trimethylsilyl)ethyl group; Desilylation; DFT calculations; N Nitrosocarbamates; X ray structures

Indexed keywords

AMIDE; CARBAMIC ACID DERIVATIVE; FLUORIDE; NITROSOUREA DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CONFORMATION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DESILYLATION; GEOMETRY; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS;

EID: 18144396541     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.044     Document Type: Article

References (40)

1. V. Benin, P. Kaszynski, and G. Radziszewski J. Am. Chem. Soc. 124 2002 14115 14126
2. J. Thiele, and A. Lachman Justus Liebigs Ann. Chem. 288 1895 304 311
3. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 1999 Wiley New York pp 64, 399-400
4. W. Yang, and M. Koreeda J. Am. Chem. Soc. 116 1994 10793 10794
5. M.L. Hamm, R. Cholera, C.L. Hoey, and T.J. Gill Org. Lett. 6 2004 3817 3820
6. T. Wada, and M. Sekine Tetrahedron Lett. 35 1994 757 760
7. J.C. Bottaro, P.E. Penwell, and R.J. Schmitt J. Am. Chem. Soc. 119 1997 9405 9410
8. L.H. Sommer, and J. Rockett J. Am. Chem. Soc. 73 1951 5130 5134
9. S. Jew, H.G. Park, H. Park, M. Park, and Y. Cho Tetrahedron Lett. 31 1990 1559 1562
10. M. Nagel, and H.-J. Hansen Helv. Chim. Acta 83 2000 1022 1045
11. Schirlin, D.; Collard, J.- N.; Danzin, C. (Merrell Dow Pharmaceuticals Inc.) USA. Eur. Pat. Appl. EP0291787, 1988, p 32.
12. S.T. Waddell, and G.M. Santorelli Tetrahedron Lett. 37 1996 1971 1974
13. P. Romea, F. Urpi, and J. Vilarassa J. Org. Chem. 54 1989 3209 3211
14. C.G. Overberger, and J.-P. Anselme J. Org. Chem. 28 1963 592 593
15. K. Prout, J. Fail, S. Hernandez-Cassou, and F.M. Miao Acta Crystallogr.. B38 1982 2176 2181
16. A.D. Becke Phys. Rev. A 38 1988 3098 3100
17. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
18. M.J. Frisch, J.A. Pople, and J.S. Binkley J. Chem. Phys. 80 1984 3265 3269
19. N. Nakayama, and O. Kikuchi J. Mol. Struct. (Theochem) 536 2001 213 218
20. J.K. Snyder, and L.M. Stock J. Org. Chem. 45 1980 886 891
21. E.H. White, and C.A.J. Aufedermarsh J. Am. Chem. Soc. 83 1961 1174 1178
22. R.W. Darbeau, E.V. Perez, J.I. Sobieski, W.A. Rose, M.C. Yates, B.J. Boese, and N.R. Darbeau J. Org. Chem. 66 2001 5679 5686
23. K. Yamaguchi, and G. Matsumura Acta Crystallogr. C48 1992 1051 1054
24. A. Hantzsch, M. Schumann, and A. Egler Chem. Ber. 32 1899 1703 1716
25. S.S. Xantheas, and T.H. Dunning Jr J. Phys. Chem. 98 1994 13489 13497
26. S.S. Xantheas J. Phys. Chem. 100 1996 9703 9713
27. O.M. Cabarcos, C.J. Weinheimer, J.M. Lisy, and S.S. Xantheas J. Chem. Phys. 110 1999 5 8
28. A.S. Pilcher, H.L. Ammon, and P. DeShong J. Am. Chem. Soc. 117 1995 5166 5167
29. D.P. Cox, J. Terpinski, and W. Lawrynowicz J. Org. Chem. 49 1984 3216 3219
30. A.S. Pilcher, and P. DeShong J. Org. Chem. 61 1996 6901 6905
31. B. Gold, and W.B. Linder J. Am. Chem. Soc. 101 1979 6772 6773
32. R.A. Moss J. Org. Chem. 31 1966 1082 1087
33. A.L. Wilds, and A.L.J. Meader J. Org. Chem. 13 1948 763 779
34. W.W. Hartman, and R. Phillips Organic Syntheses Collect. Vol. II 1943 Wiley New York p 464
35. W.W. Hartman, and M.R. Brethen Organic Syntheses Collect. Vol. II 1943 Wiley New York p 278
36. R.A. Moss Tetrahedron Lett. 7 1966 711 718
37. 3) δ 154.0, 64.3, 40.7, 29.0, 20.0, 14.3, 13.5.
38. J. Busch-Petersen, Y. Bo, and E.J. Corey Tetrahedron Lett. 40 1999 2065 2068
39. SHELXTL, version 6.10; Bruker AXS, Inc.: Madison, WI, 2000.
40. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, R.C. Gaussian, Inc.: Wallingford, CT, 2004.