Appl. Sci. 2012, 2(1), 129-138; doi:10.3390/app2010129
Article

Computational Study on the Acid Catalyzed Reactions of Fluorine-Containing 2,4-Dialkoxy-3,4-dihydro-2H-pyrans with Aromatic Compounds

Received: 14 January 2012; in revised form: 7 February 2012 / Accepted: 13 February 2012 / Published: 24 February 2012
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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.
Abstract: The reaction of 2,4-diethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyran (1) with aromatic compounds in refluxing acetonitrile in the presence of p-toluenesulfonic acid gave the mixture of 4-aryl-2-trifluoromethyl-4H-pyrans (3) and 6-aryl-1,1,1-trifluorohexa-3,5-dien-2-ones (4). In contrast, the same reaction carried out in trifluoroacetic acid at ambient temperature afforded 4-aryl-2-ethoxy-6-trifluoromethyl-3,4-dihydro-2H-pyrans (2) selectively. These two types of reactions giving quite different products under each condition were studied on the basis of DFT calculations. Moreover, the proposed mechanism for the reaction of 5-trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyran (5) with aromatic compounds affording butadiene derivatives (6) exclusively was also discussed based on the calculations and comparison with the reactivity of pyrylium intermediate (7).
Keywords: fluorine-containing dihydropyrans; fluorine-containing 1,3-butadienes; acid catalyzed reaction; DFT calculation
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MDPI and ACS Style

Ota, N.; Kamitori, Y.; Shirai, R.; Hatakenaka, M.; Okada, E. Computational Study on the Acid Catalyzed Reactions of Fluorine-Containing 2,4-Dialkoxy-3,4-dihydro-2H-pyrans with Aromatic Compounds. Appl. Sci. 2012, 2, 129-138.

AMA Style

Ota N, Kamitori Y, Shirai R, Hatakenaka M, Okada E. Computational Study on the Acid Catalyzed Reactions of Fluorine-Containing 2,4-Dialkoxy-3,4-dihydro-2H-pyrans with Aromatic Compounds. Applied Sciences. 2012; 2(1):129-138.

Chicago/Turabian Style

Ota, Norio; Kamitori, Yasuhiro; Shirai, Ryusuke; Hatakenaka, Mizuki; Okada, Etsuji. 2012. "Computational Study on the Acid Catalyzed Reactions of Fluorine-Containing 2,4-Dialkoxy-3,4-dihydro-2H-pyrans with Aromatic Compounds." Appl. Sci. 2, no. 1: 129-138.

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