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

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

1
Graduate School of Science and Technology, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
2
Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
3
Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
*
Authors to whom correspondence should be addressed.
Received: 14 January 2012 / Revised: 7 February 2012 / Accepted: 13 February 2012 / Published: 24 February 2012
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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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). View Full-Text
Keywords: fluorine-containing dihydropyrans; fluorine-containing 1,3-butadienes; acid catalyzed reaction; DFT calculation 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.

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