Issue Date: October 29, 2007
Schizoid Chemical Reactivity
In what appears to be a chemical first, two equivalent functional groups in the same molecule are reported to undergo different reactions with the same reagent (Chem. Commun. 2007, 4227). Ulrich Siemeling, Dag Rother, and Clemens Bruhn of the University of Kassel, in Germany, discovered this "schizoid behavior" when reacting 1,1′-diisocyanoferrocene with gold acetylide. Isocyano groups (-N≡C) are important in organic synthesis, metal-coordination chemistry, and surface science. One of the isocyano groups undergoes an addition reaction in which the gold atom coordinates linearly to the terminal carbon atom, as expected (shown, top; X = ferrocenyl). But the other isocyano group undergoes an insertion reaction in which the terminal carbon atom slides into the Au-C bond (bottom), which is a very rare occurrence for gold and the isocyano group. The actual product formed is a trimer, which has an unusual structure because of weak attractive interactions between neighboring gold atoms. The researchers are systematically exploring the chemistry of the intriguing schizoid reaction "to identify the method in this madness," they write.
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