Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds

Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowd...

Full description

Saved in:
Bibliographic Details
Published in:ChemistryOpen (Weinheim) 2023-02, Vol.12 (2), p.e202300007-n/a
Main Authors: Plater, M. John, Harrison, William T. A.
Format: Article
Language:English
Subjects:
Aniline
aposafranone
Benzene
Chromatography
chromophores
Free radicals
Hydrocarbons
Iodine
NMR
Nuclear magnetic resonance
phenazinone
safranone
Solvents
X-ray crystallography
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1‐methyl and N‐phenyl groups. The UV/Vis absorption maxima are in the range 530–545 nm. A crowded donor‐acceptor aposafranone has been characterised by an X‐ray single crystal structure determination. Steric bulk is believed to stabilise free radical intermediates and facilitate a free radical cyclisation pathway forming the chromophore.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.202300007