A reação de Diels-Alder entre p-Benzoquinonas 1,3-Pentadienos-1-Substituídos

• Ano de defesa: 2004
• Autor(a) principal: Finelli, Fernanda Gadini
• Orientador(a): Brocksom, Ursula
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de São Carlos
• Programa de Pós-Graduação: Programa de Pós-Graduação em Química - PPGQ
• País: BR
• Palavras-chave em Português: Síntese orgânica; Reações multicomponente; Sesquiterpenos Eudesmanos; Coeficiente orbitalar; Diels-Alder; para-Benzoquinonas
• Área do conhecimento CNPq: CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: https://repositorio.ufscar.br/handle/20.500.14289/6552

In this dissertation, studies are described on the cycloaddition of 1-silyloxypentadiene- 1,3 and 1-acylamino-pentadiene-1,3 with alkylated para-benzoquinones. The first methodology involves cycloaddition reactions of dienes 51, 115 and 116, under catalysis and thermolysis conditions, with para-benzoquinones 37, 42 and 43.The second methodology involves the preparation of the diene in situ from the α,β-unsaturated aldehyde (80) and the amide (81) in the presence of the p-benzoquinones 37, 42 and 43.Theoretical calculations have been carried out on the frontier orbital energies, and the coefficients of the dienes and dienophiles employed in this work, and then compared with the experimental results. Cycloadduct 52 has been studied chemically with the objective of attaining the functionality of common eudesmane sesquiterpenes.