Journal
SCIENCE
Volume 340, Issue 6128, Pages 57-60Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1231247
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- John Simon Guggenheim Memorial Foundation
- Johns Hopkins University
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Halonium ions, in which formally positively charged halogens (chlorine, bromine, and iodine) are equivalently attached to two carbon atoms through three-center bonds, are well established in the synthetic chemistry of organochlorides, bromides, and iodides. Mechanistic studies of these ions have generated numerous insights into the origins of stereoselectivity in addition and displacement reactions. However, it has not been clear whether fluorine can form a halonium ion in the same manner. We present chemical and theoretical evidence for the transient generation of a true symmetrical fluoronium ion in solution from an appropriately configured precursor.
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