Synthetic uses of thioesters of trifluoromethylated acids. Part 2: Reactions with alkenes

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3069-3072

  Billard, Thierry ^a   Roques, Nicolas ^a   Langlois, Bernard R ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

(trifluoromet hyl)alkanes; Photolysis; Trifluoromethanethiosulfonates; Trifluorothioacetates

Indexed keywords

ACETIC ACID DERIVATIVE; FLUORINE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOESTER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; METHYLATION; PHOTOLYSIS; SYNTHESIS;

EID: 0034701466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00337-3     Document Type: Article

References (11)

1. (a) Filler, R.; Kobayashi, Y.; Yagulpolskii, Y. L. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier: Amsterdam, 1993.
2. (b) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
3. (c) Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II. A Critical Review; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
4. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555-6666.
5. Billard, T.; Langlois, B. R.; Large, S.; Anker, D.; Roidot, N.; Roure, P. J. Org. Chem. 1996, 61, 7545.
6. Billard, T.; Roques, N.; Langlois, B. R. J. Org. Chem. 1999, 64, 3813-3820.
7. Thioesters and alkenes, dissolved in 20 mL of dichloromethane, were introduced in a quartz cylindrical flask (plane faces in vertical position), fitted with a vertical reflux condenser. Air was blown off from this solution with nitrogen. Then, the stirred reaction mixture was illuminated by a mercury vapor lamp (Phillips HPK125, 125 W), through the plane walls of the reactor.
8. Fossey, J.; Lefort, D.; Sorba, J. Les Radicaux Libres en Chimie Organique; Masson: Paris, 1993; p. 73.
9. Billard, T.; Langlois, B. Tetrahedron 1999, 55, 8065-8074.
10. Roques, N. Ph.D. Dissertation, University Claude Bernard-Lyon I, Villeurbanne (France), 1996.
11. 19F NMR, mass spectrum and by analogy with the literature (Brookes, C. J.; Coe, P. L.; Pedler, A. E.; Tatlow, J. C. J. Chem. Soc., Perkin Trans. 1 1978, 202-209.