Synthesis of heterocyclic compounds by radical electrochemical approach in environmentally friendly media

Radical cyclisation is rapidly becoming an important method for the formation of cyclic systems. Hence, some electrochemical results obtained in the study of electroreductive intramolecular cyclisation of ethyl 2-bromo-3-(3,4-methylenedioxophenyl)-3-(propargyloxy)propanoate (1a), [1-bromo-2-methoxy-...

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Bibliographic Details
Main Author: Duñach, E. (author)
Other Authors: Esteves, Ana Paula (author), Neves, C. S. S. (author), Medeiros, Maria José (author)
Format: conferencePaper
Language:eng
Published: 2008
Online Access:http://hdl.handle.net/1822/25658
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/25658
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Summary:Radical cyclisation is rapidly becoming an important method for the formation of cyclic systems. Hence, some electrochemical results obtained in the study of electroreductive intramolecular cyclisation of ethyl 2-bromo-3-(3,4-methylenedioxophenyl)-3-(propargyloxy)propanoate (1a), [1-bromo-2-methoxy-2-(prop-2’-ynyloxy) ethyl] benzene (1b) and 1-[2-bromo-2-phenyl-1-(prop-2’-ynyloxy)ethyl]-4-methoxybenzene (1c) promoted by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetra-decane)nickel(I), [Ni(tmc)]+, electrogenerated at glassy carbon cathodes in ethanol, ethanol / water and microemulsions made with cationic and anionic surfactants are presented. The results obtained indicate that the reaction proceeds via cleavage of the carbon–bromine bond to form a radical intermediate that undergoes cyclization on the unsaturated C-C bond to afford the substituted tetrahydrofurans.