Investigations into Competitive Cycloaddition/Cyclization or Elimination from 1,1-Dimethyl-propargylcarbamates of Anilines
HÉROGUEZ, Valérie
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
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Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering
Language
en
Article de revue
This item was published in
Australian Journal of Chemistry. 2011, vol. 64, n° 2, p. 166-173
CSIRO Publishing
English Abstract
The copper-catalyzed reaction of 1,1-dimethyl-O-propargyl aniline carbamates was studied and revealed the unexpected formation of oxazolidin-2-ones and alkylamines. An in-depth study of the reaction conditions showed that ...Read more >
The copper-catalyzed reaction of 1,1-dimethyl-O-propargyl aniline carbamates was studied and revealed the unexpected formation of oxazolidin-2-ones and alkylamines. An in-depth study of the reaction conditions showed that the formation of these products was highly dependent on the solvent, copper catalyst and aniline substituents. The reaction can be oriented towards oxazolidinones in pyridine and alkylamines in ethanol, whereas cycloaddition can be achieved in dry tetrahydrofuran.Read less <
English Keywords
ISOCYANATES
4-METHYLENE-2-OXAZOLIDINONES
ALCOHOLS
CLICK CHEMISTRY
CATALYZED CYCLIZATION
PROPARGYL CARBONATES
CONVENIENT SYNTHESIS
MILD CONDITIONS
AMINES
BOND
Origin
Hal imported