Selective radical cyclisation of propargyl bromoethers to tetrahydrofuran derivatives via electrogenerated nickel(I) tetramethylcyclam

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 tetraa...

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Bibliographic Details
Main Author: Esteves, Ana Paula (author)
Other Authors: Ferreira, Elisabete Carvalho N. (author), Medeiros, Maria José (author)
Format: article
Language:eng
Published: 2007
Subjects:
Electrosynthesis
Electrocatalytic reduction
Intramolecular cyclisation
Nickel(I) tetramethylcyclam
Science & Technology
Online Access:https://hdl.handle.net/1822/6603
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/6603
Description
Summary: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.

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