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
|