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A Preferred Disrotatory 4 n Electron Möbius Aromatic Transition State for a Thermal Electrocyclic Reaction
Author(s) -
Mauksch Michael,
Tsogoeva Svetlana B.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200806009
Subject(s) - conrotatory and disrotatory , electrocyclic reaction , thermal , electron , state (computer science) , computational chemistry , photochemistry , chemistry , physics , thermodynamics , computer science , organic chemistry , quantum mechanics , ring (chemistry) , algorithm
Not forbidden : Thermal 4 n electron electrocyclic reactions of Hückel topology structures proceed via “allowed” conrotatory pathways. However, for a Möbius topology, the Woodward–Hoffmann rules may be reversed and a “forbidden” disrotatory pathway can be preferred as shown theoretically for dodecahexaene 1 that transforms via a Heilbronner–Möbius aromatic transition structure 2 into a cyclic polyene 3 .