Abstract
The 1,3-dipolar cycloadditions of azomethine ylides to aromatic dipolarophiles are reviewed and discussed. The reaction proceeds with stabilized and non-stabilized azomethine ylides, although most studies have been with non-stabilized systems. While simple benzene derivatives do not readily undergo such 1,3-dipolar cycloaddition reactions, the dipolarophilic character of benzene emerges when the benzenoid nucleus is embedded within a polycyclic aromatic hydrocarbon, tethered with the azomethine ylide (an intramolecular process) or substituted with highly electron withdrawing nitro groups. Heteroaromatic systems display similar tendencies towards such cycloaddition processes. The review closes with a consideration of the mechanism of the reactions.
Highlights
A large and structurally diverse range of aromatic compounds are available for use as starting materials in organic synthesis and find use in numerous fine chemical, pharmaceutical and agrochemical products
These methods include processes resulting in aromatic carbon-hydrogen functionalization,[1,2,3,4,5] and processes resulting in loss of the aromatic system, i.e. ‘dearomatization’ processes.[6,7]
Azomethine ylides, which contain four electrons distributed over the π orbitals of a C-N-C group, are examples of bent allyl anion-type 1,3dipoles.[41]
Summary
A large and structurally diverse range of aromatic compounds are available for use as starting materials in organic synthesis and find use in numerous fine chemical, pharmaceutical and agrochemical products.
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