Preparation of (Z)-1-halo-1-alkenes and (Z)-1-halo-2-alkoxy-1-alkenes using Cr(II/III) and Fe(0)

Synlett

Volumn , Issue 16, 2006, Pages 2652-2654

  Falck, J R ^a   He, Anyu ^a   Bejot, Romain ^b   Mioskowski, Charles ^b  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkenyl halides; Carbenoids; Chromium; Enol ethers

Indexed keywords

1,1,1 TRIHALOALKANE DERIVATIVE; ALKANE DERIVATIVE; CHROMIUM; IRON; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 33750063988     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951467     Document Type: Article

References (17)

1. For examples of alternative vinyl halide syntheses, see: (a) Gosney, I.; Lloyd, S. In Comprehensive Organic Functional Group Transformations, Vol. 1; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon Press: New York, 1995, 719.
2. (b) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965.
3. (c) Brown, H. C.; Blue, C. D.; Nelson, D. J.; Bhat, N. G. J. Org. Chem. 1989, 54, 6064.
4. (d) Takai, K.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4389.
5. (e) Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1981, 22, 315.
6. (f) Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. Angew. Chem. Int. Ed. 1999, 38, 2384.
7. For examples of 1-halo-2-alkoxyvinyl ether syntheses, see: (a) Alks, V.; Sufrin, J. R. Synth. Commun. 1989, 19, 1479.
8. (b) Stalick, W. M.; Khorrami, A.; Hatton, K. S. J. Org. Chem. 1986, 51, 3577.
9. (c) Pirrung, M. C.; Hwu, J. R. Tetrahedron Lett. 1983, 24, 565.
10. (d) Taskinen, E.; Sainio, E. Tetrahedron 1976, 32, 593.
11. (e) Corey, E. J.; Hegedus, L. S. J. Am. Chem. Soc. 1969, 91, 1233.
12. Baati, R.; Barma, D. K.; Krishna, U. M.; Mioskowski, C.; Falck, J. R. Tetrahedron Lett. 2002, 43, 959.
13. Mn(0) has been utilized previously to regenerate Cr(II): Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
14. Baati, R.; Barma, D. K.; Falck, J. R.; Mioskowski, C. J. Am. Chem. Soc. 2001, 123, 9196.
15. Namba, K.; Cui, S.; Wang, J.; Kishi, Y. Org. Lett. 2005, 7, 5417.
16. Nakagawa, M.; Saito, A.; Soga, A.; Yamamoto, N.; Taguchi, T. Tetrahedron Lett. 2005, 46, 5257.
17. 3): δ = 192.6, 164.3, 147.6, 130.5, 127.2, 114.2, 83.8, 74.0, 55.7.