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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Detalhes bibliográficos
Autor principal: Duñach, E. (author)
Outros Autores: Esteves, Ana Paula (author), Neves, C. S. S. (author), Medeiros, Maria José (author)
Formato: conferencePaper
Idioma:eng
Publicado em: 2008
Texto completo:http://hdl.handle.net/1822/25658
País:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/25658
Descrição
Resumo: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.