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Dicyclopropa[ a,c ]naphthalene: a Compound Capable of Existence?
Author(s) -
Brinker Udo H.,
Wüster Hartmut,
Maas Gerhard
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.198705771
Subject(s) - naphthalene , adduct , strain (injury) , chemistry , medicinal chemistry , base (topology) , aromaticity , computational chemistry , organic chemistry , mathematics , molecule , biology , mathematical analysis , anatomy
The limits for the existence of aromatic compounds are apparently reached in the attempt to generate the title compound 1 . If the experiments are carried out in the presence of 1,3‐diphenylisobenzofuran, two bis‐adducts are isolated, which are formally derived from la . However, they are evidently formed by stepwise additions to the double bonds generated successively by reaction of the educt 2 with base. Apparently, the great increase in strain energy in 1 cannot be compensated by the increase in aromatic stabilization. The answer to the question posed in the title is therefore probably not.