A Novel Route to Polyfluorinated Alka-2E,4E-dienes

Abstract

Treatment of (Z)-α-Fluoro-β-trifluoromethylvinylstannanes 3 with n-butyllithium gave tetrafluoropropene anion 4, which was reacted with α,β-unsaturated aldehydes affording 6. With or without isolation of 6, DAST was added and reacted with 6 to give polyfluorinated alka-2E,4E isomers, exclusively. It is noteworthy that the migration of the double bond occurred only at the non-fluorine-containing one.

Key words

polyfluorinated alka-2E,4E isomers - (diethylamino)sulfur trifluoride - polyfluorinated diallylic alcohols - double bond migration

References

• 1a Filler R. Kobayashi Y. Biomedical Aspects of Fluorine Chemistry   Elsevier; Amsterdam: 1982. 
• 1b Welch JT. Tetrahedron  1982,  43:  3123 
• 1c Welch JT. Eswarakrishnam S. Fluorine in Biorganic Chemistry   Wiley; New York: 1991. 
• 1d Resnati G. Tetrahedron  1993,  49:  9385 
• 2a Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications   Filler R. Kobayashi Y. Yagupolski LM. Elsevier; Amsterdam: 1993. 
• 2b Inventory of Industrial Fluorobiochemicals   Becker A. Eyrolles; Paris: 1996. 
• 2c Smart BE. Chem. Rev.  1996,  96:  1555 
• 2d Resnati G. Soloshnok VA. Tetrahedron  1996,  52:  1 
• 2e Hibi S. Kikuchi K. Yoshimura H. Nagai M. Tai K. Hida T. J. Med. Chem.  1998,  41:  3245 
• 3a Wnuk SF. Ro BO. Valdez CA. Lewandowska E. Valdez NX. Sacasa PR. Yin D. Zhang JS. Borchardt RT. Declercq E. J. Med. Chem.  2002,  45:  2651 
• 3b Smith AB. Brandt BM. Org. Lett.  2001,  3:  1685 
• 4a Rozhkov RV. Larock RC. Org. Lett.  2003,  5:  797 
• 4b Nayek A. Drew MGB. Ghosh S. Tetrahedron  2003,  59:  5175 
• 4c Singh SB. Graham PL. Reamer RA. Cordingley MG. Bioorg. Med. Chem. Lett.  2001,  11:  3143 
• 5a He ZJ. Yi CS. Donaldson WA. Org. Lett.  2003,  5:  1567 
• 5b Sibi MP. Aasmul M. Hasegawa H. Subramarian T. Org. Lett.  2003,  5:  2883 
• 5c Capaccio CAI. Varela O. J. Org. Chem.  2002,  67:  7839 
• 5d Minami T. Okamoto H. Ikeda S. Tanaka R. Ozawa F. Yoshifuji M. Angew. Chem. Int. Ed.  2001,  40:  4501 
• 5e Liepins V. Backvall JE. Org. Lett.  2001,  3:  1861 
• 6 Yoshimatsu M. Sugimoto T. Okada N. Kinoshita S. J. Org. Chem.  1999,  64:  5162 
• 7a Zhang X. Lu L. Burton DJ. Collect. Czech. Chem. Commun.  2002,  67:  1247 
• 7b Thadani AN. Rawal VH. Org. Lett.  2002,  4:  4317 
• 7c Xu JJ. Burton DJ. Tetrahedron Lett.  2002,  43:  4565 
• 7d Shen QL. Hammond GB. Org. Lett.  2001,  3:  2213 
• 8 Ikedas S. Acc. Chem. Res.  2000,  33:  511 
• 9 Trost BM. Pinkerton AB. Seidel M. J. Am. Chem. Soc.  2001,  123:  12466 
• 10 Shen Y. Ni J. Li P. Sun J. J. Chem. Soc., Perkin Trans. 1  1999,  509 
• 11 Shen Y. Zhang Y. Sun J. Synthesis  2002,  2674 
• 12a Shen Y. Acc. Chem. Res.  1998,  31:  584 ; and the references cited therein
• 12b Shen Y. Li P. Ni J. Sun J. J. Org. Chem.  1998,  63:  9396 
• 12c Shen Y. Jiang G. Sun J. J. Chem. Soc., Perkin Trans. 1  1999,  3495 
• 12d Shen Y. Wang G. Ni J. Sun J. Synthesis  2003,  1574 
• 13a Middleton WJ. J. Org. Chem.  1975,  40:  574 
• 13b Blackburn GM. Kent DE. J. Chem. Soc., Chem. Commun.  1981,  511 
• 14 Shen Y. Wang G. Synthesis  2003,  209 
• 15 Lee SH. Achwartz J. J. Am. Chem. Soc.  1986,  108:  2445 
• 16 Shen Y. Wang G. Org. Lett.  2002,  4:  2083