Diels–Alder Adducts on the  b  Side of Naphthalene: Rapid Cycloreversion of  o ‐Quinodimethanes | Zendy

Grimme Wolfram | Zendy; Höner Peter | Zendy; Kämmerling Heinz Theo | Zendy; Waldraff Robert | Zendy; Wirz Jakob | Zendy

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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.

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