The Chemical Behavior of Multibridged [2n] Cyclophanes
- 1 July 1982
- journal article
- review article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 21 (7) , 469-480
- https://doi.org/10.1002/anie.198204691
Abstract
Multibridged [2n] 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 [2n]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.Keywords
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