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Promotion of Organic Reactions by Non‐Benzenoid Carbocyclic Aromatic Ions
Author(s) -
Lyons Demelza J. M.,
Crocker Reece D.,
Blümel Marcus,
Nguyen Thanh V.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605979
Subject(s) - aromaticity , electrophile , ion , chemistry , conjugated system , bromide , nucleophile , antiaromaticity , computational chemistry , reactivity (psychology) , organic chemistry , molecule , catalysis , medicine , alternative medicine , pathology , polymer
The first three primary members of the non‐benzenoid carbocyclic aromatic ion family, namely cyclopropenium, cyclopentadienide, and cycloheptatrienium (tropylium) ions, have planar cyclic structures with (4 n +2)π electrons in fully conjugated systems. They fulfill Hückel's rule for aromaticity and hence possess extraordinary stability. Since the historic discovery of tropylium bromide in the late 19th Century, these non‐benzenoid aromatic ions have attracted a lot of attention because of their unique combination of stability and reactivity. The charge on the aromatic ions makes them more prone to nucleophilic/electrophilic reactions than the neutral benzenoid counterparts. Within the last seven years, there has been a large number of investigations in utilizing aromatic ions to mediate organic reactions. This Review highlights these recent developments and discusses the potential of aromatic ions in promoting synthetically useful organic transformations.