Stereoselective Preparation of (E)-(1,2-Difluoro-1,2-ethenediyl) Bis[tributylstannane] and Stereospecific Synthesis of (E)-1,2-Difluorostilbenes

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1483-1485

  Liu, Qibo ^a   Burton, Donald J ^a  

^a The University of Iowa   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001411181     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025686+     Document Type: Article

References (20)

1. Sato, K.; Inoue, S.; Machida, K. U.S. Patent 5,380,461 (Cl. 252-299.61, Co9K19/34), 10 Jan 1995; JP Appl. 90/96, 259, 13 Apr 1990; CA 122: P252298x.
2. Inoue, S.; Asahi, M.; Honda, K. Rep. Asahi. Glass Found. 1995, 37,
3. Jing, N.; Lemal, D. M. J. Org. Chem. 1994, 59, 1844.
4. McGrath, T. F.; Levine, R. J. Am. Chem. Soc. 1955, 77, 4168.
5. Dixon, S. J. Org. Chem. 1956, 21, 400.
6. Kam, T.; Lim, T. J. Chem. Soc., Perkin Trans. 2 1993, 147.
7. For selected papers for the synthesis and synthetic applications of fluorinated organometallic reagents, see: (a) Burton, D. J.; Yang, Z.; Morken, P. A. Tetrahedron 1994, 50, 2993.
8. (b) Burton, D. J. In Synthetic Fluorine Chemistry; Olah, G. A., Chambers, R. D., Prakash, G. K. S., Eds.; Wiley: New York, 1992; pp 205-206.
9. (c) Burton, D. J. Yang, Z. In Chemistry of Organic Fluorine Compounds II; Hudlicky, M., Pavlath, A. E., Eds.; Washington, DC; 1995; PP 670-728.
10. (d) Burton, D. J. Yang, Z. Tetrahedron 1992, 48, 189.
11. (e) Xue, L.; Lu, L.; Pedersen, S.;. Liu, Q.; Narske, R., Burton, D. J., Tetrahedron Lett. 1996, 37, 1921.
12. (f) Xue, L.; Lu, L.; Pedersen, S.; Liu, Q.; Narske, R.; Burton, D. J., J. Org. Chem. 1997, 62, 1064.
13. (g) Fontana, S. A.; Davis, C. R.; He, Y.; Burton, D. J. Tetrahedron 1996, 52, 37.
14. (h) Davis, C. R.; Burton, D. J. Tetrahedron Lett. 1996, 37, 7237.
15. (i) Davis, C. R.; Burton, D. J. J. Org. Chem. 1997, 62, 9217.
16. (j) Liu, Q.; Burton, D. J. Tetrahedron Lett. 2000, 41, 8045.
17. 8 352.0498, obsd 352.0511.
18. Attempts to prepare unsymmetrical stilbenes via sequential coupling of the bis-stannane were unsuccessful.
19. 11
20. Liu, Q. The University of Iowa, unpublished work.