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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Preparation of a silanone through oxygen atom transfer to a stable cyclic silylene
Michael M Linden1, Hans Peter Reisenauer1, Dennis Gerbig1
1Institute of Organic Chemistry, Justus-Liebig-University, Heinrich-Buff-Ring 58, 35392 Giessen (Germany).
Abstract:
We report the evaporation of a stable cyclic silylene and its oxidation (with ozone or N2 O) through oxygen atom transfer to form the corresponding silanone under matrix isolation conditions. As uncomplexed silanones are rare owing to their very high reactivity, this method provides an alternative route to these sought-after molecules. The silanone, as well as a novel bicyclic silane with a bridgehead silicon atom derived from an intramolecular silylene CH bond insertion, were characterized by comparison of high-resolution infrared spectra with density functional theory (DFT) computations at the M06-2X/cc-pVDZ level of theory.
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