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Synthesis 2006(2): 339-343
DOI: 10.1055/s-2005-918508
DOI: 10.1055/s-2005-918508
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Diels-Alder Reactions of Dienophiles with Pentafluoro-λ6-sulfanyl (SF5) Moiety
Further Information
Received
27 June 2005
Publication Date:
21 December 2005 (online)
Publication History
Publication Date:
21 December 2005 (online)
Abstract
This paper describes a convenient and efficient synthesis of new dienophiles containing a pentafluoro-λ6-sulfanyl moiety. These compounds react readily with both cyclic and aliphatic electron-releasing dienes, leading to the formation of Diels-Alder cycloadducts.
Key words
alkenes - Diels-Alder reaction - fluorine - sulfur
- 1
Brant P.Berry AD.DeMarco RA.Carter FL.Fox WB.Hashmall JA. J. Electron Spectrosc. Relat. Phenom. 1981, 22: 119 - 2
Lentz D.Seppelt K. In Chemistry of Hypervalent CompoundsAkiba K. John Wiley and Sons; New York: 1999. p.295-325 -
3a
Casado M,LeRoy P, andPevere V. inventors; Eur. Pat. Appl. EP668269A1 950823. ; Chem. Abstr. 1996, 125, 256707y -
3b
Phillips WG.Rejda-Health JM. Pestic. Sci. 1993, 38: 1 -
4a
Sitzmann ME.Gilligan WH.Ornellas DL.Thrasher JS. J. Energ. Mater. 1990, 8: 352 -
4b
Sitzmann ME. J. Fluorine Chem. 1991, 52: 195 -
4c
Sitzmann ME.Gilardi RD. J. Fluorine Chem. 1993, 63: 203 -
4d
Bovin JL. inventors; Can. Patent 1085875. ; Chem. Abstr. 1981, 94, 156285 - 5
Bartell LS.Bradford WF. J. Mol. Struct. 1977, 37: 113 - 6
Cinich J.Ludvig MM.Paudler WW.Gard GL.Shreeve JM. Inorg. Chem. 1985, 24: 3668 - 7
Hoover FW.Coffman DD. J. Org. Chem. 1964, 29: 3567 - 8
Brel VK.Zefirov NS. In Chemistry of Hypervalent CompoundsAkiba K. John Wiley and Sons; New York: 1999. p.389-408 -
9a
Trushkov IV.Brel VK. Tetrahedron Lett. 2005, 46: 4777 -
9b
Winter R.Gard GL. J. Fluorine Chem. 1994, 66: 109 - 10
Brel VK. Synthesis 2005, 1245 - 11
Klauck A.Seppelt K. Angew. Chem. 1994, 106: 98 - 12
Pattison LM.Stothers LB.Woolford RG. J. Am. Chem. Soc. 1959, 78: 2252 - 13
Winter R.Gard GL. J. Fluorine Chem. 2000, 102: 79 - 14
Winter R.Nixon PG.Gard GL.Rabford DH.Holcomb NR.Grainger DW. J. Fluorine Chem. 2001, 107: 23 - 15
Perrin DD.Armarego WLF.Perrin DR. Purification of Laboratory Chemicals Pergamon Press; Oxford: 1988.