Formação sequencial de ligações carbono-carbono/carbono-selênio mediada por cloreto férrico e dicalcogenetos de diorganoíla: síntese e reatividade de 2-organocalcogenil-naftalenos

• Ano de defesa: 2017
• Autor(a) principal: Recchi, Ana Maria Spohr
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; Brasil; Química; UFSM; Programa de Pós-Graduação em Química; Centro de Ciências Naturais e Exatas
• Palavras-chave em Português: Ciclização intramolecular; Dicalcogenetos de diorganoíla; Alquinois; Intramolecular cyclization; Diorganyl dichalcogenides; Alkynols; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/14460

In the present study, a series of aryl alkynols functionalized was subjected to intramolecular cyclization reaction promoted by iron(III) chloride and diorganyl dichalcogenides allowing the synthesis of 2-organoselenyl-naphthalenes. The mutual action between the diorganyl dichalcogenide and iron (III) chloride, in a 0.6: 0.75 mole ratio, was essential for the achievement of the products in good yields. The cyclization reaction tolerated a variety of functional groups, such as electron-donating group, electron-withdrawing groups and bulky groups. It was obtained the naphthalene derivatives exclusively via 6-endo-dig cyclization, giving thirty new compounds in 45-90% yields. In addition, using these compounds it was possible to carry out a selenium-lithium exchange reaction, giving the lithium intermediate derivatives, which were captured by electrophiles, leading to five new compounds in 45-96% yields.