info:eu-repo/semantics/article
Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans
Fecha
2011-02Registro en:
Brasca, Romina; Kneeteman, Maria Nelida; Mancini, Pedro Maximo Emilio; Fabian, Walter M. F.; Comprehensive DFT study on site-, regio-, and stereoselectivity of diels-alder reactions leading to 5-hydroxybenzofurans; Wiley VCH Verlag; European Journal of Organic Chemistry; 4; 2-2011; 721-729
1434-193X
CONICET Digital
CONICET
Autor
Brasca, Romina
Kneeteman, Maria Nelida
Mancini, Pedro Maximo Emilio
Fabian, Walter M. F.
Resumen
Diels-Alder reactions between the substituted furans 1a-1c and Danishefsky's diene (2), yielding 5-hydroxybenzofurans, were studied by density functional theory [B3LYP/6-31G(d) level] in benzene as solvent (SP/CPCM). The mechanistic details of these reactions, especially with respect to regio-, site-, and stereochemistry were analyzed in detail. Moreover, the extrusion of nitrous acid from the Diels-Alder cycloadducts and the formation of the aromatic products were also explained in order to give a total description of the complete domino processes. Some Diels-Alder reactions leading to 5-hydroxybenzofurans were studied at the B3LYP/6-31G(d) level of theory in benzene as solvent (SP/CPCM). DFT calculations on the transition structures were carried out for all the possible reaction channels (site, regio-, and stereoisomeric channels were included in this study). Additionally, a description of the complete domino processes was performed.