Polyimidazoles via aromatic nucleophilic displacement

Details Polyimidazoles via aromatic nucleophilic displacement Polyimidazoles via aromatic nucleophilic displacement

1990-04-12

1991-11-19

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548336, 548337, 548342, C07F 928, C07D21170, C07D21182

Patent

active

050668110

ABSTRACT:
Polyimidazoles (Pl) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenyl)imidazole monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The reactions are carried out in polar aprotic solvents such as N,N-dimethylacetamide, sulfolane, N-methylpyrroldinone, dimethylsulfoxide, or diphenylsulfone using alkali metal bases such as potassium carbonate at elevated temperature under nitrogen. The di(hydroxyphenyl)imidazole monomers are prepared by reacting an aromatic aldehyde with a dimethoxybenzil or by reacting an aromatic dialdehyde with a methoxybenzil in the presence of ammonium acetate. The di(methoxyphenyl)imidazole is subsequently treated with aqueous hydrobromic acid to give the di(hydroxyphenyl)imidazole monomer. This synthetic route has provided high molecular weight Pl of new chemical structure, is economically and synthetically more favorable than other routes, and allows for facile chemical structure variation due to the availability of a large variety of activated aromatic dihalides and dinitro compounds.

REFERENCES:
Radlmann et al., Chem. Abstracts, vol. 75, No. 26, 152165u.
Kuenzel et al., Chem. Abstracts., vol. 72, No 4, 68047n.
Farberfabriken, Chem. Abstracts, vol. 72, No. 12, 56103q.

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