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The Triplet Surface of the Zimmerman Di‐π‐Methane Rearrangement of Dibenzobarrelene
Author(s) -
Matute Ricardo A.,
Houk Kendall N.
Publication year - 2012
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.201208002
Subject(s) - diradical , alkene , state (computer science) , methane , chemistry , photochemistry , physics , computer science , atomic physics , singlet state , organic chemistry , algorithm , catalysis , excited state
High‐level calculations : The Zimmerman di‐π‐methane rearrangement of dibenzobarrelene occurs via a triplet state to form dibenzosemibullvalene, overcoming two barriers connecting two biradicals. The shape of the triplet potential‐energy surface shows that the rearrangement involves two transition states. The first triplet diradical intermediate may bypass in the passive of the alkene triplet to the final intermediate (see picture).