Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid

Tetrahedron Letters

Volumn 49, Issue 16, 2008, Pages 2638-2641

  Klein, Suzane M ^a   Zhang, Cungen ^b   Jiang, Yu Lin ^a  

^a EAST TENNESSEE STATE UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

Alcohols; Alkyl bromides; Alkyl iodides; Hydriodic acid; Hydriodination; Hydrobromination; Hydrogen bromide

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; BROMINE; BUTANE; HYDROBROMIC ACID; IODIDE; IODINE; METHANE;

ARTICLE; BROMINATION; CHEMICAL REACTION; IODINATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 40849101523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.106     Document Type: Article

References (33)

1. Trewick S.C., Henshaw T.F., Hausinger R.P., Lindahl T., and Sedgwick B. Nature 419 (2002) 174-178
2. Krafft M.E., Seibert K.A., Haxell T.F.N., and Hirosawa C. Chem. Commun. (2005) 5772-5774
3. Zhong M., and Robins M.J. J. Org. Chem. 71 (2006) 8901-8906
4. Friestad G.K., Marie J.-C., and Deveau A.M. Org. Lett. 6 (2004) 3249-3252
5. Reinhard R., and Schmidt B.F. J. Org. Chem. 63 (1998) 2434-2441
6. Smith T.H., Fujiwara A.N., and Henry D.W. J. Med. Chem. 22 (1979) 40-44
7. Loksha Y.M., El-Badawi M.A., El-Barbary A.A., Pedersen E.B., and Nielsen C. Arch. Pharm. 336 (2003) 175-180
8. Andrus M.B., Hicken E.J., Stephens J.C., and Bedke D.K. J. Org. Chem. 70 (2005) 9470-9479
9. DeGraw J.I., Colwell W.T., Crase J., Smith R.L., Piper J.R., Waud W.R., and Sirotnak F.M. J. Med. Chem. 40 (1997) 370-376
10. Liang F., Sadana A.K., Peera A., Chattopadhyay J., Gu Z., Hauge R.H., and Billups W.E. Nano Lett. 4 (2004) 1257-1260
11. Yu B., Edstrom W.C., Benach J., Hamuro Y., Weber P.C., Gibney B.R., and Hunt J.F. Nature 439 (2006) 879-884
12. Cao C., Kwon K., Jiang Y.L., Drohat A.C., and Stivers J.T. J. Biol. Chem. 278 (2003) 48012-48020
13. Takahashi K., Kawazoe Y., Sakumi K., Nakabeppu Y., and Sekiguchi M. J. Biol. Chem. 263 (1998) 13490-13492
14. Myers L.C., Wagner G., and Verdine G.L. J. Am. Chem. Soc. 117 (1995) 10749-10750
15. Azhar K.F., Qudrat-e-Khuda M., and Zuberi R. J. Chem. Soc. Pakistan 24 (2002) 57-61
16. Schiffmann D., Eder E., Neudecker T., and Henschler D. Cancer Lett. 20 (1983) 263-269
17. Lastovskii R.P., and Temkina V.Ya. Khim. Prom. (1958) 219-221
18. Chem. Abstr. 53 (1958) 6353
19. Taguchi, N.; Takahashi, M. JP 2005024073, 2005; Chem. Abstr. 2005, 142, 170502.
20. Weber, L. DE 3201535, 1983; Chem. Abstr. 1983, 99, 104767.
21. Berlak M.C., and Gerrard W. J. Chem. Soc. (1949) 2309-2312
22. Stone H., and Shechter H. J. Org. Chem. 15 (1950) 491-495
23. Khan K.M., Zia-Ullah, Perveen S., Maharvi G.M., Shah S.T.A., Ambreen N., Choudhary M.I., Atta-ur-Rahman, and Voelter W. Lett. Org. Chem. 2 (2005) 644-647
24. Namavari M., Satyamurthy N., Phelps M.E., and Barrio J.R. Tetrahedron Lett. 31 (1990) 4973-4976
25. Brown H.C., Rathke M.W., Rogic M.M., and De Lue N.R. Tetrahedron 44 (1988) 2751-2762
26. Ren R.X., and Wu J.X. Org. Lett. 3 (2001) 3727-3728
27. Magovern R.L., Ries H.C., and Breier I.L. Chem. Abstr. 56 (1962) 29850
28. Agreda, V. H.; Steinmetz, G. R. U.S. Patent 4,976,947, 1990; Chem. Abstr. 1990, 114, 125353.
29. Vlasov G.A., Bushina N.D., Buravtseva G.I., and Mukhametshina L.V. Zh. Prikl. Khim. 73 (2000) 682-683
30. Chem. Abstr. 133 (2000) 152581
31. Coumbarides G.S., Eames J., and Weerasooriya N. J. Labelled Comp. Radiopharm. 46 (2003) 291-296
32. Slegers G., Sambre J., Goethals P., Vandecasteele C., and Van Haver D. Appl. Radiat. Isot. 37 (1986) 279-292
33. Tang J., Qi X., Mercola D., Han J., and Chen G. J. Biol. Chem. 280 (2005) 23910-23917