computational study on the acid catalyzed reactions of fluorine-containing 2,4-dialkoxy-3,4-dihydro-2h-pyrans with aromatic compounds计算研究含氟酸催化反应2,4-dialkoxy-3,4-dihydro-2h-pyrans芳香族化合物.pdfVIP
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computational study on the acid catalyzed reactions of fluorine-containing 2,4-dialkoxy-3,4-dihydro-2h-pyrans with aromatic compounds计算研究含氟酸催化反应2,4-dialkoxy-3,4-dihydro-2h-pyrans芳香族化合物
Appl. Sci. 2012, 2, 129-138; doi:10.3390/app2010129 OPEN ACCESS applied sciences ISSN 2076-3417 /journal/applsci Article Computational Study on the Acid Catalyzed Reactions of Fluorine-Containing 2,4-Dialkoxy-3,4-dihydro-2H-pyrans with Aromatic Compounds Norio Ota 1, Yasuhiro Kamitori 2,*, Ryusuke Shirai 3, Mizuki Hatakenaka 2 and Etsuji Okada 2,* 1 Graduate School of Science and Technology, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan; E-Mail: norio.ota@shionogi.co.jp 2 Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan; E-Mail: 119t453t@stu.kobe-u.ac.jp 3 Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan; shirai@ * Authors to whom correspondence should be addressed; E-Mails: kamitori@kobe-u.ac.jp (Y.K.); okaetsu@kobe-u.ac.jp (E.O.); Tel.: +81-78-803-6163; Fax: +81-78-803-6163. Received: 14 January 2012; in revised form: 7 February 2012 / Accepted: 13 February 2012 / Published: 24 February 2012 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-
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