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Diels–Alder Adducts on the b Side of Naphthalene: Rapid Cycloreversion of o ‐Quinodimethanes
Author(s) -
Grimme Wolfram,
Höner Peter,
Kämmerling Heinz Theo,
Waldraff Robert,
Wirz Jakob
Publication year - 1989
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.198913531
Subject(s) - adduct , naphthalene , chemistry , photochemistry , resonance (particle physics) , benzene , derivative (finance) , alicyclic compound , diels–alder reaction , medicinal chemistry , polymer chemistry , organic chemistry , physics , catalysis , particle physics , financial economics , economics
The cycloreversion of the naphthalene adduct 1 is extremely fast, since, in contrast to reaction of adducts of type 2 , the full resonance energy is released. The most unstable alicyclic Diels–Alder adduct of type 1 is the benzene derivative, compound 3 , for which the free energy of cycloreversion is only 12.2 kcal mol −1 . The corresponding gain in resonance energy is 50.5 kcal mol −1 . The thermally and photochemically accessible adducts 1 can be trapped by Diels–Alder reactions owing to their o ‐quinodimethane structural elements.