Theoretical study of the Diels-Alder reaction between o-benzoquinone and norbornadiene
Por:
Quijano-Quiñones R.F., Quesadas-Rojas M., Cuevas G., Mena-Rejón G.J.
Publicada:
1 ene 2013
Resumen:
The reaction between norbornadiene and o-benzoquinone is an important step in polyalicyclic rigid structures synthesis. It has been considered that this reaction is an example of Diels-Alder (DA) and hetero-Diels-Alder (HDA) cycloadditions with o-benzoquinone acting as diene (forming C-C bonds) and heterodiene (forming O-C bonds). We have performed a Density Functional Theory study of this reaction, employing B3LYP, mPW1PW91, and B1B95 functionals and 6-31G(d,p) and 6-31+G(d,p) Gaussian type basis sets. The results indicate that Diels-Alder is a feasible mechanism for both reactions, but should not be the main route to the formation of products with C-C bonds. © Published under licence by IOP Publishing Ltd.
Filiaciones:
Quijano-Quiñones R.F.:
Laboratorio de Química Farmacéutica, Facultad de Química, Universidad Autónoma de Yucatán, calle 41 No. 421 x 26 y 28 col. Industrial, C.P. 97150, Mérida, Yucatán, Mexico
Quesadas-Rojas M.:
Laboratorio de Química Farmacéutica, Facultad de Química, Universidad Autónoma de Yucatán, calle 41 No. 421 x 26 y 28 col. Industrial, C.P. 97150, Mérida, Yucatán, Mexico
Cuevas G.:
Instituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, C.P. 04510 México D.F., Mexico
Mena-Rejón G.J.:
Laboratorio de Química Farmacéutica, Facultad de Química, Universidad Autónoma de Yucatán, calle 41 No. 421 x 26 y 28 col. Industrial, C.P. 97150, Mérida, Yucatán, Mexico
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