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Mechanism of scandium ion catalyzed diels-alder reaction of anthracenes with Methyl Vinyl Ketone

Journal of Physical Chemistry A, ISSN: 1089-5639, Vol: 109, Issue: 14, Page: 3174-3181
2005
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Article Description

Rates of Diels-Alder cycloadditions of anthracenes with methyl vinyl ketone (MVK) are accelerated significantly by the presence of scandium triflate [Sc(OTf)]. Sc(OTf) also promotes photoinduced electron-transfer reactions from various electron donors to MVK significantly. Comparison of the promoting effect of Sc(OTf) in photoinduced electron-transfer reactions of MVK with the catalytic effect of Sc(OTf) in the Diels-Alder reaction of 9,10-dimethylanthracene with MVK has revealed that the MVK-Sc(OTf) complex is a reactive intermediate in both the Diels-Alder and photoinduced electron-transfer reactions. The observed second-order rate constants of the Sc(OTf)-catalyzed Diels-Alder reactions of anthracenes with MVK are by far larger than those expected from the observed linear Gibbs energy relation for the Diels-Alder reactions of anthracenes with stronger electron acceptors than MVK, which are known to proceed via electron transfer. This indicates that the Sc(OTf) -catalyzed Diels-Alder reactions of anthracenes with MVK does not proceed via an electron-transfer process from anthracences to the MVK-Sc(OTf) complex. © 2005 American Chemical Society.

Bibliographic Details

Fukuzumi, Shunichi; Yuasa, Junpei; Miyagawa, Toshio; Suenobu, Tomoyoshi

American Chemical Society (ACS)

Chemistry

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