Electrophilic addition of chlorine (Cl2) or bromine (Br2) to 4-methoxy-1,1,2-trifluorobut-1-ene (1) did not give rearranged products.  This is in contrast to reaction of Cl2 or Br2  with 1,1,2-trifluorobut-1-ene-4-ol (2) where 27 and 38 percent rearranged products are found.  Ionic addition of Cl2 to 4-bromo-1 and 4-iodo-1,1,2-trifluorobut-1-ene 4 and 5 gave lesser amounts of rearranged products.  Rearranged products were not formed for bromination of alkenes 4 or 5.  The hydrocarbon alkene 6 gave less rearranged products from halogenation than its 1,1,2-trifluoroalkene analogue 2.

Reaction of chlorine and bromine with 4-methoxy- and 4-hydroxy-1,1,2-trifluoro-but-1-ene

239th National Meeting (2010)

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