A Fast, High-Yield Preparation of Vicinal Dinitro Compounds Using HOF·CH3CN

Journal of Organic Chemistry

Volumn 68, Issue 23, 2003, Pages 9170-9172

  Golan, Elizabeth ^a   Rozen, Shlomo ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN-TRANSFER AGENTS;

CHEMICAL BONDS; CHEMICAL REACTIONS; ISOTOPES; OXYGEN;

AROMATIC COMPOUNDS;

1,2 DIAMINOPROPANE; 1,2 DINITROPROPANE; DIAMINE; FLUORINE; NITRO DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG; VICINAL DINITRO DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; OXIDATION; OXYGEN TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 0242576088     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030217m     Document Type: Article

References (33)

1. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
2. Korenblum, N. Aldrichimica Acta 1990, 23 (3), 71.
3. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550.
4. Camps, P.; Munoz-Torrero, D. Tetrahedron Lett. 1994, 35, 3187.
5. Wade, P. A.; Kondracki, P. A.; Carrol, P. J. J. Am. Chem. Soc. 1991, 113, 8807.
6. Baldock, H.; Levy, N.; Scaife, C. W. J. Chem. Soc. 1949, 2627.
7. Dave, P. R.; Axenrod, T.; Qi, L.; Bracuti, A. J. Org. Chem. 1995, 60, 1895 and references therein.
8. Rozen, S.; Brand, M. Angew. Chem., Int. Ed. Engl. 1986, 25, 554.
9. (a) Rozen, S.; Kol, M. J. Org. Chem. 1990, 55, 5155.
10. (b) Hung, M. H.; Smart, B. E.; Feiring, A. E.; Rozen, S. J. Org. Chem. 1991, 56, 6, 3187.
11. (c) Rozen, S.; Bareket, Y.; Dayan, S. Tetrahedron Lett. 1996, 37, 531.
12. (d) Dayan, S.; Ben-David, I.; Rozen, S. J. Org. Chem. 2000, 65, 8816.
13. Rozen, S.; Bareket, Y.; Kol, M. Tetrahedron 1993, 49, 8169.
14. Rozen, S.; Dayan, S.; Bareket, Y. J. Org. Chem. 1995, 60, 8267.
15. Dayan, S.; Kol, M.; Rozen, S. Synthesis 1999, 1427.
16. (a) Rozen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457.
17. (b) Toyota, A.; Ono, Y.; Chiba, J.; Sugihara, T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 703.
18. (a) Kol, M.; Rozen, S. J. Chem. Soc., Chem. Commun. 1991, 567.
19. (b) Rozen, S.; Kol, M. J. Org. Chem. 1992, 57, 7342.
20. (c) Dirk, S. M.; Mickelson, E. T.; Henderson, J. C.; Tour, J. M. Org. Lett. 2000, 2, 3405.
21. (a) Rozen, S. Acc. Chem. Res. 1996, 29, 243.
22. (b) Rozen, S. Pure Appl. Chem. 1999, 71, 481.
23. Rozen, S.; Bar-Haim, A.; Mishani, E. J. Org. Chem. 1994, 59, 1208.
24. Levy, N.; Scaife, C. W. J. Chem. Soc. 1946, 1093.
25. Sreekumar, R.; Padmakumar, R.; Rugmini, P. Tetrahedron Lett. 1998, 39, 2695.
26. The racemic 11 has been made by Korenblum nitro synthesis: Crombie, L.; Roughley, B. S. Tetrahedron 1986, 42, 3147. Obviously, such synthesis is bound to lead to racemic compounds only.
27. (a) Dagan, S.; Amirav, A. J. Am. Soc. Mass Spectrom. 1995, 6, 120.
28. (b) Amirav, A.; Gordin, A.; Tzanani, N. Rapid Commun. Mass Spectrom. 2001, 15, 811.
29. Rozen, S.; Golan, E. Eur. J. Org. Chem. 2003, 1915.
30. (a) Dagan, S.; Amirav, A. J. Am. Soc. Mass Spectrom. 1996, 7, 550.
31. (b) Fialkov, A. B.; Amirav, A. Rapid Commun. Mass Spectrom. 2003, 17, 1326.
32. Fischer, A.; Henderson, G. N.; Iyer, L. M. Can. J. Chem. 1985, 63, 2390.
33. Kametani, T.; Shio, M. J. Heterocycl. Chem. 1971, 8, 545.