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Intramolecular [4 + 2]‐Cycloreversion of the Two Symmetrical Homobasketenes
Author(s) -
Grimme Wolfram,
Mauer Wolfgang,
Sarter Christian
Publication year - 1985
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.198503311
Subject(s) - intramolecular force , benzene , cyclopentadiene , strain (injury) , chemistry , ring strain , decomposition , tricyclic , aromaticity , photochemistry , strain energy , stereochemistry , ring (chemistry) , physics , molecule , organic chemistry , anatomy , thermodynamics , medicine , finite element method , catalysis
The strain energy of the educts and the aromaticity of the products are the driving force for the [4 + 2]‐cycloreversion of the homobasketene 1 . The tricyclic intermediate 2 decomposes to benzene and cyclopentadiene. The free energy of activation for the decomposition of basketene and its homologues is proportional to the loss of strain energy.