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Reversal of Orbital Symmetry Control in Electrocyclic Ring Closures through Craig‐Möbius Aromaticity
Author(s) -
Mauksch Michael,
Tsogoeva Svetlana B.
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201600086
Subject(s) - aromaticity , ring (chemistry) , antiaromaticity , symmetry (geometry) , computational chemistry , chemistry , homo/lumo , organic chemistry , molecule , mathematics , geometry
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.