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Organic cyclisations of propargyl and allyl bromoesters in microemulsions catalysed by electrogenerated nickel(I) tetramethylcyclam

Organic cyclisations of propargyl and allyl bromoesters in microemulsions catalysed by electrogenerated nickel(I) tetramethylcyclam
Organic cyclisations of propargyl and allyl bromoesters in microemulsions catalysed by electrogenerated nickel(I) tetramethylcyclam
While the reductive intramolecular cyclisation of propargyl and allyl bromoesters catalysed by [Ni(tmc)]+ gives good yields of the desired products using N,N-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.
electrosynthesis, microemulsions, cyclic voltammetry, alkyl bromides, reduction, unsaturated halides, vitreous carbon cathodes, complexes, electrochemical, intramolecular cyclisation, intramolecular cyclization, dimethylformamide, electrocataiytic, tetraaza macrocycle, bicontinuous microemulsion, electroreductive radical cyclization
1572-6657
131-138
Esteves, A.P.
ce887b59-6557-46b4-8247-e2f12eabf1df
Neves, C.S.
967c6448-b26a-4fa2-b9da-d104cfca3357
Medeiros, M.J.
53878fb3-634c-47cb-990c-0eb784e38c27
Pletcher, D.
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Esteves, A.P.
ce887b59-6557-46b4-8247-e2f12eabf1df
Neves, C.S.
967c6448-b26a-4fa2-b9da-d104cfca3357
Medeiros, M.J.
53878fb3-634c-47cb-990c-0eb784e38c27
Pletcher, D.
f22ebe69-b859-4a89-80b0-9e190e6f8f30

Esteves, A.P., Neves, C.S., Medeiros, M.J. and Pletcher, D. (2008) Organic cyclisations of propargyl and allyl bromoesters in microemulsions catalysed by electrogenerated nickel(I) tetramethylcyclam. Journal of Electroanalytical Chemistry, 614 (1-2), 131-138. (doi:10.1016/j.jelechem.2007.11.006).

Record type: Article

Abstract

While the reductive intramolecular cyclisation of propargyl and allyl bromoesters catalysed by [Ni(tmc)]+ gives good yields of the desired products using N,N-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.

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More information

Published date: 15 March 2008
Keywords: electrosynthesis, microemulsions, cyclic voltammetry, alkyl bromides, reduction, unsaturated halides, vitreous carbon cathodes, complexes, electrochemical, intramolecular cyclisation, intramolecular cyclization, dimethylformamide, electrocataiytic, tetraaza macrocycle, bicontinuous microemulsion, electroreductive radical cyclization

Identifiers

Local EPrints ID: 54449
URI: http://eprints.soton.ac.uk/id/eprint/54449
ISSN: 1572-6657
PURE UUID: e52d945e-2c05-432b-b434-0dd7ce4983b8

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Date deposited: 06 Aug 2008
Last modified: 13 Mar 2019 20:38

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