Synthesis of 2-pentafluorosulfanylnaphthalene

Tetrahedron Letters

Volumn 48, Issue 8, 2007, Pages 1325-1326

  Dolbier Jr , William R ^a   Mitani, Akira ^a   Warren, Robin D ^a  

^a University of Florida   (United States)

Author keywords

Naphthalene; Pentafluorosulfanyl group; SF5 Group; SF5Cl

Indexed keywords

BENZENE DERIVATIVE; ETHYLENE; NAPHTHALENE DERIVATIVE; TETRAZINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CYCLOADDITION; ELIMINATION REACTION; HEATING; SYNTHESIS;

EID: 33846362127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.123     Document Type: Article

References (13)

1. Bowden R.D., Comina P.J., Greenhall M.P., Kariuki B.M., Loveday A., and Philp D. Tetrahedron 56 (2000) 3399-3408
2. Sergeeva T.A., and Dolbier Jr. W.R. Org. Lett. 6 (2004) 1417-1419
3. Winter R.W., and Gard G.L. J. Fluorine Chem. 125 (2004) 549-552
4. 5Cl to 1,4-dihydronaphthalene, followed by elimination and aromatization steps.
5. Lal, G. S.; Minnich, K. E. US Patent Application Publication No. 2006/0069285 A1.
6. 13C NMR, d 31.4, 49.6, 122.6, 123.8, 140.1.
7. Johnson R.P., Exarchou A., Jefford C.W., and Hahn R.C. J. Org. Chem. 42 (1977) 3758-3759
8. Miller R.G., and Stiles M. J. Am. Chem. Soc. 85 (1963) 1798-1800
9. Ait-Mohand S., and Dolbier Jr. W.R. Org. Lett. 4 (2002) 3013-3015
10. 19F NMR, d +60.2 (d, J = 153 Hz, 4F), +84.4 (pent, J = 153 Hz, 1F).
11. 13C NMR, 134.1, 132.2, 129.45, 128.83, 128.79, 127.83, 127.69, 126.61 (pent, J = 4.6 Hz), 122.50 (pent, J = 4.4 Hz).
12. Zhai Y.-A., Ghiviriga I., Battiste M.A., and Dolbier Jr. W.R. Synthesis (2004) 2747-2750
13. 5S: C, 47.25; H, 2.78. Found: C, 46.98; H, 2.57.