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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig-Möbius Aromaticity
Michael Mauksch1, Svetlana B Tsogoeva2
1Department of Chemistry and Pharmacy, Institute of Theoretical Chemistry, Computer Chemistry Center, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Nägelsbachstrasse 25a, 91052, Erlangen, Germany. michael.mauksch@fau.de.
Abstract:
Experimentalists are challenged to find the organometallic thermal electrocyclizations that are computationally predicted to proceed with opposite stereoselectivity compared to their metal-free parent 4n and 4n+2 π-electron systems. While ring closure of, for example, s-cis-butadiene proceeds conrotatory, an iron alkyl complex formed by replacement of a (CH) unit by an [FeH] metal fragment results in a disrotatory electrocyclization.
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