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The Chemical Behavior of Multibridged [2 n ] Cyclophanes
Author(s) -
Kleinschroth Jürgen,
Hopf Henning
Publication year - 1982
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.198204691
Subject(s) - isomerization , nitration , chemistry , electrophilic aromatic substitution , aromaticity , benzene , electrophile , halogenation , cyclophane , cleavage (geology) , ionic bonding , molecule , acylation , friedel–crafts reaction , medicinal chemistry , organic chemistry , ion , materials science , fracture (geology) , composite material , catalysis
Multibridged [2 n ] cyclophanes comprise a novel class of aromatic compounds, in which two benzene rings are connected by three up to a maximum of six ethano bridges. Compared to classical nonannelated arenes, their most distinct chemical property is the ease with which, particularly the higher‐bridged homologs, take part in addition reactions (Diels‐Alder additions, hydrogenations, and ionic additions). On the other hand, the typical regenerative behavior of aromatic molecules is not fully suppressed in the [2 n ]cyclophanes as evidenced by such typical electrophilic aromatic substitution reactions as bromination, Friedel‐Crafts acylation, and nitration. Besides these reactions in which the benzene rings are either destroyed or retained, reactions at and with the ethano bridges, e.g. their cleavage, isomerization, and functionalization can also occur.