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A Mild, Thermal Pentafulvene‐to‐Benzene Rearrangement
Author(s) -
Finke Aaron D.,
Haberland Sophie,
Schweizer W. Bernd,
Chen Peter,
Diederich François
Publication year - 2013
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.201304767
Subject(s) - benzene , fulvene , polar , reactivity (psychology) , ring (chemistry) , chemistry , photochemistry , computational chemistry , mechanism (biology) , thermal , organic chemistry , thermodynamics , physics , quantum mechanics , medicine , alternative medicine , pathology
Walk this way : More than 40 years after the discovery that fulvene can thermally rearrange to benzene at high temperatures, it has been found that 6,6‐dicyanopentafulvenes can rearrange quantitatively to 1,3‐ and 1,4‐dicyanobenzenes under mild conditions in polar aprotic solvents. A polar “ring‐walk” mechanism is proposed to explain this unprecedented reactivity.