Distillable ionic liquids for a new multicomponent reaction

Adducts of dimethylamine and carbon dioxide form a "distillable ionic liquid" (DIMCARB) that may used as both a reaction medium and catalyst in the direct, atom-economical synthesis of useful synthetic building blocks, such as mono-condensed α,β-unsaturated ketones. The utilization of such...

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Bibliographic Details
Published inPure and applied chemistry Vol. 79; no. 11; pp. 1869 - 1877
Main Authors Rosamilia, Anthony E., Strauss, Christopher R., Scott, Janet L.
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.11.2007
Walter de Gruyter GmbH
Subjects
Adducts
Aniline
Carbon dioxide
Catalysis
Chemical synthesis
Condensates
Coordination compounds
DIMCARB
green chemistry
Ionic liquids
Ions
Ketones
Solvents
substituted anilines
sustainability
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Summary:Adducts of dimethylamine and carbon dioxide form a "distillable ionic liquid" (DIMCARB) that may used as both a reaction medium and catalyst in the direct, atom-economical synthesis of useful synthetic building blocks, such as mono-condensed α,β-unsaturated ketones. The utilization of such building blocks in the synthesis of two new classes of versatile macrocycles, by a sequence of condensation reactions (H O by-product), is described. Investigation into the mechanism of action of DIMCARB catalysis and observation of an aniline impurity arising from a competing reaction sequence led to development of a new multicomponent reaction for the direct preparation of 2- or 4-substituted anilines. Some of the macrocycles and anilines are, respectively, supramolecular host compounds and ligands for the preparation of metal complexes.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200779111869