Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig-Möbius Aromaticity.

Chemphyschem

Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054, Erlangen, Germany.

Published: April 2016

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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http://dx.doi.org/10.1002/cphc.201600086DOI Listing

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