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Radical Reactions of a Stable N-Heterocyclic Silylene: EPR Study and DFT Calculation

Summary: Radical Reactions of a Stable N-Heterocyclic Silylene: EPR Study and DFT
Boris Tumanskii,*, Pauline Pine, Yitzhak Apeloig, Nicholas J. Hill, and Robert West*,
Department of Chemistry and the Lise Meitner-MinerVa Center for Computational Quantum Chemistry,
Technion-Israel Institute of Technology, Haifa 32000, Israel, and Department of Chemistry,
UniVersity of Wisconsin, Madison, Wisconsin 53706
Received February 17, 2004; E-mail: tboris@tx.technion.ac.il; west@chem.wisc.edu
Chemical species which involve divalent silicon atoms are key
intermediates in numerous thermal and photochemical reactions of
organosilicon compounds.1 The field of stable silylenes commenced
with the synthesis of stable N-heterocyclic compounds 1, 2, and 3,
and has led to an elaborate chemistry.2,3
These silylenes act as Lewis bases, with the lone pair on silicon
serving as the electron donor, for example in silylene-transition
metal complexes.4,5 According to spectroscopic studies, the stable
silylene 1 behaves electronically like compounds of trivalent
phosphorus.6 Thus, it could be expected that stable silylenes, such
as phosphites or phosphines7 (eq 1) might react with free radicals
to form radical intermediates (eq 2).8
We present here preliminary results of EPR studies of adducts


Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology


Collections: Chemistry