Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO

Journal of the American Chemical Society

Volumn 135, Issue 9, 2013, Pages 3355-3358

  Maity, Soham ^a   Manna, Srimanta ^a   Rana, Sujoy ^a   Naveen, Togati ^a   Mallick, Arijit ^b   Maiti, Debabrata ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL FORMATION; STEREO-SELECTIVE; STEREOSELECTIVE MANNER;

NITRATION; STEREOSELECTIVITY;

OLEFINS;

ALKENE; NITRITE; SILVER NITRITE; TEMPOL; UNCLASSIFIED DRUG;

ARTICLE; MASS FRAGMENTOGRAPHY; NITRATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALKENES; CYCLIC N-OXIDES; MOLECULAR STRUCTURE; NITRITES; NITRO COMPOUNDS; SILVER; STEREOISOMERISM;

EID: 84874858953     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja311942e     Document Type: Article

References (37)

1. Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751
2. Bui, T.; Syed, S.; Barbas, C. F. J. Am. Chem. Soc. 2009, 131, 8758
3. Ishii, T.; Fujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558
4. Huang, H. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170
5. Tripathi, C. B.; Kayal, S.; Mukherjee, S. Org. Lett. 2012, 14, 3296
6. Evans, D. A.; Mito, S.; Seidel, D. J. Am. Chem. Soc. 2007, 129, 11583
7. March, J. Advanced Organic Chemistry, 3 rd ed.; John Wiley & Sons: New York, 1985.
8. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989.
9. Albrecht, L.; Dickmeiss, G.; Acosta, F. C.; Rodriguez-Escrich, C.; Davis, R. L.; Jorgensen, K. A. J. Am. Chem. Soc. 2012, 134, 2543
10. Liu, Y. K.; Nappi, M.; Arceo, E.; Vera, S.; Melchiorre, P. J. Am. Chem. Soc. 2011, 133, 15212
11. Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338
12. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137
13. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447
14. Nair, D. K.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4580
15. Corma, A.; Serna, P.; Garcia, H. J. Am. Chem. Soc. 2007, 129, 6358
16. Martin, N. J. A.; Ozores, L.; List, B. J. Am. Chem. Soc. 2007, 129, 8976
17. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: Amsterdam, 2005.
18. Fioravanti, S.; Pellacani, L.; Tardella, P. A.; Vergari, M. C. Org. Lett. 2008, 10, 1449
19. Kancharla, P. K.; Reddy, Y. S.; Dharuman, S.; Vankar, Y. D. J. Org. Chem. 2011, 76, 5832
20. Taniguchi, T.; Fujii, T.; Ishibashi, H. J. Org. Chem. 2010, 75, 8126
21. Tinsley, S. W. J. Org. Chem. 1961, 26, 4723
22. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294
23. Sy, W. W.; By, A. W. Tetrahedron Lett. 1985, 26, 1193
24. Campos, P. J.; Garcia, B.; Rodriguez, M. A. Tetrahedron Lett. 2000, 41, 979
25. Jovel, I.; Prateeptongkum, S.; Jackstell, R.; Vogl, N.; Weckbecker, C.; Beller, M. Adv. Synth. Catal. 2008, 350, 2493
26. Mukaiyama, T.; Hata, E.; Yamada, T. Chem. Lett. 1995, 505
27. Suzuki, H.; Mori, T. J. Org. Chem. 1997, 62, 6498
28. Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199
29. Manna, S.; Maity, S.; Rana, S.; Agasti, S.; Maiti, D. Org. Lett. 2012, 14, 1736
30. Vogler, T.; Studer, A. Synthesis-Stuttgart 2008, 1979
31. Tebben, L.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 5034
32. Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901
33. He, Z. H.; Kirchberg, S.; Frohlich, R.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 3699
34. Climent, M. J.; Corma, A.; Iborra, S. Chem. Rev. 2011, 111, 1072
35. Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8221
36. Hartmann, M.; Li, Y.; Studer, A. J. Am. Chem. Soc. 2012, 134, 16516
37. Experimental details of the structure determination can be found in the Supporting Information. CCDC-905717 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data- request/cif.