Quantum chemical studies on the mechanistic aspects of tandemsequential cycloaddition reactions of cyclooctatetraene with ester andnitrones

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dc.contributor.authorOpoku, Ernest
dc.contributor.authorTia, Richard
dc.contributor.authorAdei, Evans
dc.date.accessioned2020-07-08T10:56:49Z
dc.date.accessioned2023-04-19T02:05:27Z
dc.date.available2020-07-08T10:56:49Z
dc.date.available2023-04-19T02:05:27Z
dc.date.issued2019-07-05
dc.descriptionAn article published by Elsevier Inc. and also available at https://doi.org/10.1016/j.jmgm.2019.06.019en_US
dc.description.abstractThe mechanisms of the tandem sequential [4þ2]/[3þ2] and [3þ2]/[4þ2] cycloaddition sequencesinvolving an ester, cyclooctatetraene (COTE), and cyclic and acyclic nitrones for the formation of a diverserange of isoxazolidine derivatives and other synthetic precursors are reported. A thorough exploration ofthe PES has characterized several regio-, stereo- and enantio-selective mechanistic channels involved inthese reactions. A perturbation molecular orbital (PMO) analysis been employed to rationalize the re-sults. It has also been found that the initial electrocyclic ring closure of the COTE is the rate-determiningstep in the tandem sequential [4þ2]/[3þ2] addition sequence. The thermolytic breakdown of thetandem adducts to subsequent monocyclic, bicyclic and tricyclic adducts occurs generally with very highactivation barriers making it an inconvenient synthetic approach. The different reactivity of all the threedouble bonds present in the dipolarophile is reported. Finally, the mechanistic possibilities of [3þ2]/[4þ2] addition sequences involving the same reaction components in the case of cyclic and acyclicnitrones are explored extensively. The results suggest a novel and convenient routes for obtainingproducts of high selectivity with less energetic requirements. In some instances, new cycloadductshitherto unreported are obtained.en_US
dc.description.sponsorshipKNUSTen_US
dc.identifier.citationE. Opoku et al. / Journal of Molecular Graphics and Modelling 92 (2019) 17e31. https://doi.org/10.1016/j.jmgm.2019.06.019en_US
dc.identifier.urihttps://ir.knust.edu.gh/handle/123456789/12653
dc.language.isoenen_US
dc.publisherElsevier Incen_US
dc.subjectIsoxazolidinesen_US
dc.subjectMechanistic studen_US
dc.subjectTandem additionen_US
dc.subjectCyclooctatetraeneen_US
dc.subjectNitronesen_US
dc.titleQuantum chemical studies on the mechanistic aspects of tandemsequential cycloaddition reactions of cyclooctatetraene with ester andnitronesen_US
dc.typeArticleen_US
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