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The Valence Tautomerism of Cyclooctatetraene
Author(s) -
Huisgen R.,
Mietzsch F.
Publication year - 1964
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196400831
Subject(s) - cyclooctatetraene , tautomer , bicyclic molecule , chemistry , valence (chemistry) , octane , adduct , computational chemistry , medicinal chemistry , organic chemistry , molecule
The Diels‐Alder adducts of cyclooctatetraene and its derivatives are derived from the bicyclo[4,2,0]octane structure. A kinetic investigation shows that the Diels‐Alder addition of dienophiles to cyclooctatetraene and phenylcyclooctatetraene is preceded by a valence tautomerism equilibrium with bicyclo[4,2,0]octa‐2,4,7‐triene or its 7‐phenyl derivative.