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The Thermal Retro[2+2+2]cycloaddition of Cyclohexane Activated by Triscyclobutenannelation: Concerted All‐Disrotatory versus Stepwise Conrotatory Pathways to Fused [12]Annulenes
Author(s) -
Eichberg Michael J.,
Houk K. N.,
Lehmann Jürg,
Leonard Philip W.,
Märker Anne,
Norton Joseph E.,
Sawicka Dorota,
Vollhardt K. Peter C.,
Whitener Glenn D.,
Wolff Stefan
Publication year - 2007
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.200702474
Subject(s) - conrotatory and disrotatory , cyclohexane , annulene , ring (chemistry) , cycloaddition , cyclobutane , chemistry , stereochemistry , organic chemistry , catalysis
All dis or all con? While benzo analogues 2 – 4 undergo cycloreversion of the central cyclohexane ring by all‐disrotatory opening, the triscyclobutenocyclohexane 1 does so by stepwise conrotatory cyclobutane rupture. This remarkable conclusion is based on DFT calculations carried out in conjunction with experiments.