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Molecules 2014, 19(2), 1763-1774; doi:10.3390/molecules19021763
Article

Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

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Received: 2 January 2014; in revised form: 15 January 2014 / Accepted: 27 January 2014 / Published: 3 February 2014
(This article belongs to the Special Issue Fluorine Chemistry)
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Abstract: The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.
Keywords: Pauson-Khand reaction; cycloadditions; regioselectivity; cyclopentenones; trifluoromethylalkynes Pauson-Khand reaction; cycloadditions; regioselectivity; cyclopentenones; trifluoromethylalkynes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Aiguabella, N.; Arce, E.M.; del Pozo, C.; Verdaguer, X.; Riera, A. Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity. Molecules 2014, 19, 1763-1774.

AMA Style

Aiguabella N, Arce EM, del Pozo C, Verdaguer X, Riera A. Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity. Molecules. 2014; 19(2):1763-1774.

Chicago/Turabian Style

Aiguabella, Nuria; Arce, Elsa M.; del Pozo, Carlos; Verdaguer, Xavier; Riera, Antoni. 2014. "Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity." Molecules 19, no. 2: 1763-1774.



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