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

Yanchang Shen; Guoping Wang

doi:10.1055/s-2004-822326

PAPER

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

Yanchang Shen*, Guoping Wang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: shenyc@mail.sioc.ac.cn;

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

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