Stereoselective Preparation of (Z)-α,β-Difluorostyrenes and Stereospecific Conversion to (E)-α,β-Difluoro-βiodostyrenes

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 9217-9222

  Davis, Charles R ^a,b   Burton, Donald J ^a  

^a E11 SSH   (United States)

^b AUGUSTANA COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA,BETA DIFLUORO BETA IODOSTYRENE; ALPHA,BETA DIFLUOROSTYRENE; IODIDE; LITHIUM DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; FLUORINATION; IODINATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0031446904     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971434o     Document Type: Article

References (19)

1. Reynolds, D. W.; Cassidy, P. E.; Johnson, C. G.; Cameron, M. L. J. Org. Chem. 1990, 55, 4448-4454.
2. Middleton, W. J.; Bingham, E. M. J. Fluorine Chem. 1983, 22, 561-574.
3. Middleton, W. J.; Metzger, D.; Snyder, J. A. J. Med. Chem. 1971, 14, 1193-1197.
4. Sevestiyan, A. P.; Fialkov, Yu. A.; Khranovskii, V. A.; Yagupolskii, L. M. Zh. Org. Khim. 1978, 14, 204-205.
5. Prober, M. J. Am. Chem. Soc. 1953, 75, 968-973.
6. Leroy, J. J. Org. Chem. 1980, 46, 206-209.
7. Martin, S.; Sauvetre, R.; Normant, J. F. Tetrahedron Lett. 1982, 23, 4329-4332.
8. Yagupolskii, L. M.; Cherednichenko, P. G.; Kremlev, M. M. J. Org. Chem. USSR (English Transl.) 1987, 23, 246-248.
9. Martin, S.; Sauvetre, R.; Normant, J. F. Tetrahedron Lett. 1983, 24, 5615-5618.
10. Davis, C. R.; Burton, D. J. Tetrahedron Lett. 1996, 37, 7237-7240.
11. Ling Xue, Ph.D. Thesis, University of Iowa, 1996; presented, in part, at the 11th ACS Winter Fluorine Conference, Abstr. No. P56.
12. Fontana, S. A.; Davis, C. R.; He, Y. H.; Burton, D. J. Tetrahedron 1996, 52, 37-44.
13. For a review, see: Burton, D. J.; Yang, Z. Y.; Morken, P. A. Tetrahedron 1994, 50, 2993-3063.
14. Hiyama, T.; Nishide, K.; Obayashi, M. Chem. Lett. 1984, 10, 1765-1768.
15. 3, unpublished results, University of Iowa.
16. Heinze, P. L.; Burton, D. J. J. Org. Chem. 1988, 53, 2714-2720.
17. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348.
18. Normant, J. F. J. Organomet. Chem. 1990, 400, 19-34.
19. Coulson, D. R. Inorg. Synth. 1972, 13, 121-124.