Organic cyclisations of propargyl and allyl bromoesters in microemulsions catalysed by electrogenerated nickel(I) tetramethylcyclam
authors Esteves, AP; Neves, CS; Medeiros, MJ; Pletcher, D
nationality International
journal JOURNAL OF ELECTROANALYTICAL CHEMISTRY
author keywords microemulsions; cyclic voltammetry; electrosynthesis; electrocataiytic reduction; intramolecular cyclisation
keywords ELECTROREDUCTIVE RADICAL CYCLIZATION; VITREOUS CARBON CATHODES; INTRAMOLECULAR CYCLIZATION; BICONTINUOUS MICROEMULSION; ELECTROCHEMICAL REDUCTION; ALKYL BROMIDES; UNSATURATED HALIDES; TETRAAZA MACROCYCLE; COMPLEXES; DIMETHYLFORMAMIDE
abstract While the reductive intramolecular cyclisation of propargyl and allyl bromoesters catalysed by [Ni(tmc)](+) gives good yields of the desired products using NN-dimethylformamide as the solvent, the use of this aprotic solvent presents practical, safety and environmental issues. This paper therefore reports the search for non-toxic alternatives, in particular the study of microemulsions prepared from water, hydrocarbons, surfactant and alcohol co-surfactant. It is shown that the [Ni(tmc)](2+)/[Ni(tmc)](+) couple is reversible in such media and that [Ni(tmc)](+) reacts rapidly with propargyl and allyl bromoesters to give excellent yields of cyclic products. Indeed, these microemulsions are convenient media for such syntheses. (c) 2007 Elsevier B.V. All rights reserved.
publisher ELSEVIER SCIENCE SA
issn 1572-6657
year published 2008
volume 614
issue 1-2
beginning page 131
ending page 138
digital object identifier (doi) 10.1016/j.jelechem.2007.11.006
web of science category Chemistry, Analytical; Electrochemistry
subject category Chemistry; Electrochemistry
unique article identifier WOS:000254428500017
  ciceco authors
  impact metrics
journal analysis (jcr 2019):
journal impact factor 3.807
5 year journal impact factor 3.519
category normalized journal impact factor percentile 70.963
dimensions (citation analysis):
altmetrics (social interaction):



 


Sponsors

1suponsers_list_ciceco.jpg