Reaction of halogens and interhalogens with 1,1,2-trifluorobut-1-ene-4-ol

CHED 428

Ryan J. Weiss, rweiss@pointloma.edu, Rachel N Jones, and Dale F. Shellhamer, dshellha@ptloma.edu. Department of Chemistry, Point Loma Nazarene University, 3900 Lomaland Dr, San Diego, CA 92106
Reactions of the halogens chlorine (Cl2), bromine (Br2), and the interhalogen iodine monochloride (ICl) with 1,1,2-trifluorobut-1-ene-4-ol were studied. Ionic reactions of halogen electrophiles give three-membered halonium ion intermediates (1) that can rearrange to give 3-halo-2,2,3-trifluorotetrahydrofurans (2). The effect that the number-4 alcohol group has on forming the five-membered rearranged products 2 is reported. These data are compared to addition of halogen electrophiles (Cl2, Br2, and ICl) to the hydrocarbon analog 3-butene-1-ol.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008