Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/6603

TitleSelective radical cyclisation of propargyl bromoethers to tetrahydrofuran derivatives via electrogenerated nickel(I) tetramethylcyclam
Author(s)Esteves, Ana Paula
Ferreira, E. C.
Medeiros, Maria José
KeywordsElectrosynthesis
Electrocatalytic reduction
Intramolecular cyclisation
Nickel(I) tetramethylcyclam
Issue date2007
PublisherElsevier
JournalTetrahedron
Citation“Tetrahedron". ISSN 0040-4020. 63:14 (Apr. 2007) 3006-3009.
Abstract(s)The controlled-potential reduction of [1-bromo-2-methoxy-2-(prop-2'-ynyloxy)ethyl]benzene(1a), 1-[2-bromo-2-phenyl-1-(prop-2'-ynyloxy)ethyl]-4-methoxybenzene (1b) and 2-bromo-3-(3',4'-dimethoxyphenyl)-propargyloxypropanamide (1c) catalysed by (1,4,8,11-tetramethyl-1,4,8,11 tetraazacyclotetradecane)nickel(I), [Ni(tmc)]+, at a vitreous carbon cathode in DMF/Et4NBF4 leads to 2-methoxy-4-methylene-3-phenyl-tetrahydrofuran (2a), 2-(4'-methoxyphenyl)-4-methylene-3-phenyl-tetrahydrofuran (2b) and 2-(3',4'-dimethoxyphenyl)-3-carbamoyl-4-methylenetetrahydrofuran (2c), respectively, in very high yields.
TypeArticle
URIhttp://hdl.handle.net/1822/6603
DOI10.1016/j.tet.2007.01.071
ISSN0040-4020
Publisher versionwww.sciencedirect.com
Peer-Reviewedyes
AccessRestricted access (UMinho)
Appears in Collections:CDQuim - Artigos (Papers)

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