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Trends in Organic Chemistry   Volumes    Volume 14 
Abstract
Reaction of halogens and interhalogens with 1,1,2-trifluorobut-1-en-4-ol and 3-butene-1-ol: A study on the rearrangement of trifluorosubstituted 3-membered halonium ions
Dale F. Shellhamer, Kevyn J. Davenport, Rachel N. Jones, Jacob J. Thorpe, Ryan J. Weiss, Victor L. Heasley
Pages: 73 - 77
Number of pages: 5
Trends in Organic Chemistry
Volume 14 

Copyright © 2010 Research Trends. All rights reserved

ABSTRACT
 
Reaction of halogen electrophiles (Cl2, Br2, or ICl) with 1,1,2-trifluorobut-1-en-4-ol (6) and 3-buten-1-ol (7) give dihalo products 9 and cyclized 3-halofurans (11). Vinyl fluorines stabilize positive charge on the carbons of the three-membered halonium ions better than hydrogen.  This is supported by the greater amount of rearranged furan products from the trifluoroalkene 6 than the hydrocarbon alkene 7.  Halonium ions from 6 and 7 are rather symmetrical except for the ionic reaction of chlorine with 6 where the three fluorines stabilize the positive charge sufficiently such that open-ion intermediates 12 and 13 are indicated.
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