The preparation of aliphatic fluorinated sulfoximines

Synthesis

Volumn , Issue 4, 2003, Pages 565-569

  Magnier, Emmanuel ^a   Wakselman, Claude ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

Author keywords

Arylations; Fluorine; Imination of sulfoxides; Sulfoximines; Sulfur

Indexed keywords

ALKYLATION; ELECTRONS; SYNTHESIS (CHEMICAL);

ALIPHATIC SERIES;

ORGANIC COMPOUNDS;

S PERFLUOROOCTYL S METHYLSULFOXIMINE; S TRIFLUOROMETHYL S OCTYLSULFOXIMINE; SULFOXIDE; SULFOXIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEGRADATION; ELECTRON TRANSPORT; FLUORINATION; MELTING POINT; REACTION ANALYSIS; SYNTHESIS;

EID: 0037241792     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37651     Document Type: Article

References (22)

1. Bentley, H. R.; Whitehead, J. K. J. Chem. Soc. (D) 1950, 2081.
2. (a) Johnson, C. R. In Comprehensive Organic Chemistry, Vol 3; Barton, D.; Ollis, W. D., Eds.; Pergamon: Oxford, 1979, 223-232.
3. (b) Johnson, C. R. Aldrichimica Acta 1985, 18, 3. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1.
4. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1.
5. Bailey, H. H. Chem. Biol. Interact. 1998, 111, 239.
6. Bolm, C.; Simić O. J. Am. Chem. Soc. 2001, 123, 2081; and references therein.
7. (a) Kondratenko, N. V.; Popov, V. I.; Radchenko, O. A.; Ignatev, N. V.; Yagupol'skii, L. M. Zh. Org. Khim. 1986, 22, 1716.
8. (b) Yagupol'skii, L. M. J. Fluorine Chem. 1987, 36, 1.
9. (a) Boiko, V. N.; Kirii, N. V.; Yagupol'skii, L. M. J. Fluorine. Chem. 1994, 67, 119.
10. (b) Bzhezovsky, V.; Penkovsky, V. Phosphorous, Sulfur Silicon Relat. Elem. 1994, 95, 413.
11. Anselmi, A.; Blazejewski, J.-C.; Tordeux, M.; Wakselman, C. J. Fluorine. Chem. 2000, 105, 41.
12. Bentley, H. R.; Whitehead, J. K. J. Chem. Soc. 1952, 1572.
13. Johnson, C. R.; Janiga, E. R. J. Am. Chem. Soc. 1973, 95, 7692.
14. We assume that the lack of reactivity is due to the poor nucleophilicity of the sulfur because of the presence of the trifluoromethyl group.
15. Kondratenko, N. V.; Radchenko, O. A.; Yagupol'skii, L. M. Zh. Org. Khim. 1984, 20, 2250.
16. Attempts at imination of sulfoxide 5 under Yagupol'skii's conditions gave rise to a complex mixture of products in a low yield. In Bentley and Whitehead's conditions no transformation of the fluorinated sulfoxide 5 was observed.
17. Craig, D.; Geach, N. J. Synlett 1993, 481.
18. Hwang, K. J. J. Org. Chem. 1986, 51, 99.
19. Mutti, R.; Winternitz, P. Synthesis 1986, 426.
20. Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169.
21. (a) Wakselman, C.; Tordeux, M.; Clavel, J.-L.; Langlois, B. J. Chem. Soc.. Chem. Commun. 1991, 993.
22. (b) Clavel, J.-L.; Langlois, B.; Nantermet, R.; Tordeux, M.; Wakselman, C. J. Chem. Soc., Perkin Trans. 1 1992, 3371.