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Mauksch M, Tsogoeva SB. Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig-Möbius Aromaticity. Chemphyschem. 2016;17(7):963-6doi: 10.1002/cphc.201600086.
Mauksch, M., & Tsogoeva, S. B. (2016). Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig-Möbius Aromaticity. Chemphyschem : a European journal of chemical physics and physical chemistry, 17(7), 963-6. https://doi.org/10.1002/cphc.201600086
Mauksch, Michael, and Tsogoeva, Svetlana B. "Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig-Möbius Aromaticity." Chemphyschem : a European journal of chemical physics and physical chemistry vol. 17,7 (2016): 963-6. doi: https://doi.org/10.1002/cphc.201600086
Mauksch M, Tsogoeva SB. Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig-Möbius Aromaticity. Chemphyschem. 2016 Apr 04;17(7):963-6. doi: 10.1002/cphc.201600086. Epub 2016 Feb 24. PMID: 26817734.
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Chemphyschem. 2016 Apr 04;17(7):963-6. doi: 10.1002/cphc.201600086. Epub 2016 Feb 24.

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

Chemphyschem : a European journal of chemical physics and physical chemistry

Michael Mauksch, Svetlana B Tsogoeva

Affiliations

  1. Department of Chemistry and Pharmacy, Institute of Theoretical Chemistry, Computer Chemistry Center, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Nägelsbachstrasse 25a, 91052, Erlangen, Germany. [email protected].
  2. 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. [email protected].

PMID: 26817734 DOI: 10.1002/cphc.201600086

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.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Möbius aromaticity; electrocyclic reactions; orbital symmetry; organometallic compounds; stereoselectivity

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