Methylation of sydnone N-oxides: Kinetic and thermodynamic control in the alkylation site of an electron-rich heterocycle

Journal of Organic Chemistry

Volumn 72, Issue 10, 2007, Pages 3625-3631

  Bohle, D Scott ^a   McQuade, Lindsey E ^a   Perepichka, Inna ^a   Zhang, Lijuan ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION PRODUCTS; DISUBSTITUTED RING NITROGEN; METHYL IODIDE; THERMODYNAMIC CONTROL;

ALKYLATION; METHYLATION; REGIOSELECTIVITY; SUBSTITUTION REACTIONS; THERMODYNAMIC PROPERTIES; X RAY DIFFRACTION;

NITROGEN COMPOUNDS;

4 METHYLCARBOXY 1,2,3 OXADIAZOLATE 3 OXIDE; DIMETHYL SULFATE; METHYL IODIDE; NITROGEN; OXIDE; OXYGEN; SULFONIC ACID DERIVATIVE; SYDNONE DERIVATIVE; TRIFLUOROMETHANEMETHYLSULFONATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ISOMER; ISOMERIZATION; KINETICS; METHYLATION; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 34248580514     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062235k     Document Type: Article

References (25)

1. Arulsamy, N.; Bohle, D. S. Angew. Chem., Int. Ed.2002, 41, 2089-2091.
2. Stewart, F. H. C. Chem. Rev. 1964, 64, 129-147.
3. Arulsamy, N.; Bohle, D. S.; Perepichka, I. Can. J. Chem. 2007, 85, 105-117.
4. Keefer, L. K.; Flippen-Anderson, J.; George, C.; Shanklin, A. P.; Dunams, T. M.; Christodoulou, D.; Saavedra, J. E.; Sagan, E. S.; Bohle, D. S. Nitric Oxide 2001, 5, 377-394.
5. Saavedra, J. E.; Bohle, D. S.; Smith, K. N.; George, C.; Deschamps, J. R.; Parrish, D.; Ivanic, J.; Wang, Y.-N.; Citro, M. L.; Keefer, L. K. J. Am. Chem. Soc. 2004, 126, 12880-12887.
6. Wang, Y.-N.; Bohle, D. S.; Bonifant, C. L.; Chmurny, G. N.; Collins, J. R.; Davies, K. M.; Deschamps, J. R.; Flippen-Anderson, J. L.; Keefer, L. K.; Klose, J. R.; Saavedra, J. E.; Waterhouse, D. J.; Parrish, D.; Ivanic, J. J. Am. Chem. Soc. 2005, 127, 5388-5395.
7. Sugihara, T.; Kuwahara, K.; Wakabayashi, A.; Takao, H.; Imagawa, H.; Nishizawa, M. Chem. Commun. 2004, 216-217.
8. Weintraub, P. M.; Bambury, R. E. Tetrahedron Lett. 1969, 579-581.
9. Baker, W.; Ollis, W. D.; Poole, V. D. J. Chem. Soc. 1949, 307.
10. Yashchunskii, V. G.; Vasil'eva, V. F.; Sheinker, Y. N. Zh. Obshch. Khim. 1962, 29, 2712.
11. Greco, C. V.; O'Reilly, B. P. Tetrahedron Lett. 1971, 3057-3060.
12. Olah, G. A.; Kelly, D. P.; Suciu, N. J. Am. Chem. Soc. 1970, 92, 3133-3137.
13. Wieland, H.; Kerr, F. N. Chem. Ber. 1930, 63, 570-579.
14. Petrie, S.; Stranger, R. Inorg. Chem. 2004, 43, 2597-2610.
15. Brouwer, A. M.; Krijnen, B. J. Org. Chem. 1995, 60, 32-40.
16. Nielsen, I. M. B. J. Phys. Chem. A 1998, 102, 3193-3201.
17. Lehn, J. M. Fortschr. Chem. Forsch. 1970, 15, 311-377.
18. Berson, J. A. Acc. Chem. Res. 1972, 5, 406-414.
19. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1994, 33, 449.
20. Arulsamy, N.; Bohle, D. S.; Imonigie, J. A.; Sagan, E. S. J. Am. Chem. Soc. 2000, 122, 5539-5549.
21. Frisch, M. J.; et al. Gaussian 98; Gaussian Inc.: Pittsburgh, PA, 1998.
22. Roothaan, C. C. J. Rev. Mod. Phys. 1951, 23, 69-89.
23. Lee, C. Y., W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
24. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
25. SHELXTL 5.10 ed.; Bruker AXS, Inc.: Madison, WI, 1997.