Preparation of SF5 aromatics by vicarious nucleophilic substitution reactions of nitro(pentafluorosulfanyl)benzenes with carbanions

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4781-4786

  Beier, Petr ^a   Pastýříková, Tereza ^a   Iakobson, George ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; BASIC MEDIA; HIGH YIELD; VICARIOUS NUCLEOPHILIC SUBSTITUTIONS;

IONS; SUBSTITUTION REACTIONS;

BENZENE;

1 NITRO 3 (PENTAFLUOROSULFANYL)BENZENE; ANION; AROMATIC COMPOUND; CARBANION; NITRO(PENTAFLUOROSULFANYL)BENZENE; NITROBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; SUBSTITUTION REACTION; SYNTHESIS; VICARIOUS NUCLEOPHILIC SUBSTITUTION;

EID: 79957855449     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200618p     Document Type: Article

References (24)

1. For reviews, see: Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004; pp 146-156.
2. Winter, R. W.; Dodean, R. A.; Gard, G. L. In ACS Symposium Series, 911: Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; American Chemical Society: Washington, DC, 2005; pp 87-118.
3. Kirsch, P.; Röschenthaler, G. V. In ACS Symposium Series, 949: Current Fluoroorganic Chemistry; Soloshonok, V. A., Mikami, K., Yamazaki, T., Welch, J. T., Honek, J. F., Eds.; American Chemical Society: Washington, DC, 2007; pp 221-243.
4. Crowley, P. J.; Mitchell, G.; Salmon, R.; Worthington, P. A. Chimia 2004, 58, 138-142
5. Kirsch, P.; Bremer, M.; Heckmeier, M.; Tarumi, K. Angew. Chem., Int. Ed. 1999, 38, 1989-1992
6. Stump, B.; Eberle, C.; Schweizer, W. B.; Kaiser, M.; Brun, R.; Krauth-Siegel, R. L.; Lentz, D.; Diederich, F. ChemBioChem 2009, 10, 79-83
7. Bowden, R. D.; Greenhall, M. P.; Moilliet, J. S.; Thomson, J. US 5741935, 1997, and WO 9705106, 1997.
8. Bowden, R. D.; Comina, P. J.; Greenhall, M. P.; Kariuki, B. M.; Loveday, A.; Philp, D. Tetrahedron 2000, 56, 3399-3408
9. Chambers, R. D.; Spink, R. C. H. Chem. Commun. 1999, 883-884
10. Umemoto, T. WO 2008/118787, 2008.
11. Sipyagin, A. M.; Bateman, C. P.; Tan, Y.-T.; Thrasher, J. S. J. Fluorine Chem. 2001, 112, 287-295
12. Sipyagin, A. M.; Enshov, V. S.; Kashtanov, S. A.; Bateman, C. P.; Mullen, B. D.; Tan, Y.-T.; Thrasher, J. S. J. Fluorine Chem. 2004, 125, 1305-1316
13. Sheppard, W. A. J. Am. Chem. Soc. 1962, 84, 3064-3072
14. Beier, P.; Pastýříková, T.; Vida, N.; Iakobson, G. Org. Lett. 2011, 13, 1466-1469
15. For reviews, see: Makosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20, 282-289
16. Makosza, M.; Wojciechowski, K. Liebig Ann. Chem. 1997, 1805-1816
17. Makosza, M. Chem. Soc. Rev. 2010, 39, 2855-2868
18. Blazej, S.; Makosza, M. Chem.-Eur. J. 2008, 14, 11113-11122
19. Makosza, M.; Golinski, J.; Baran, J. J. Org. Chem. 1984, 49, 1488-1494
20. Makosza, M.; Sienkiewicz, K.; Wojciechowski, K. Synthesis 1990, 850-852
21. Mudryk, B.; Makosza, M. Synthesis 1988, 1007-1009
22. Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094-5100
23. Zarantonello, C.; Guerrato, A.; Ugel, E.; Bertani, R.; Benerollo, F.; Milani, R.; Venzo, A.; Zaggia, A. J. Fluorine Chem. 2007, 128, 1449-1453
24. Lawrence, N. J.; Liddle, J.; Jackson, D. A. Synlett 1996, 55-56