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Electrocyclic Opening of 2,3‐Benzo‐ and 2,3;7,8‐Dibenzobicyclo[4.2.0]octa‐2,4,7‐triene;Benzoannelated Transition States
Author(s) -
Grimme Wolfram,
Lex Johann,
Schmidt Thomas
Publication year - 1987
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.198712681
Subject(s) - pericyclic reaction , chemistry , hydrocarbon , transition state , double bond , electrocyclic reaction , cope rearrangement , stereochemistry , transition (genetics) , computational chemistry , medicinal chemistry , catalysis , bicyclic molecule , organic chemistry , biochemistry , gene
Benzenoid double bonds readily participate in pericyclic reactions , but this is often masked by a rapid back reaction. It has now been possible to demonstrate this phenomenon in the case of the hydrocarbon 1 deuteriated in position 4; at 100°C, equilibrium is established between 1 and its labeled isomer 1 ′ via the o ‐quinoid intermediates 2 and 2 ′ ( K 1.13, k(100.6°C) = (7.45 ± 0.06)xl0 −5 s −1 ).