Cycloaddition Reactions of <I>N</I>-Sulfinylsulfonamides with Ketenimines
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概要
- 論文の詳細を見る
<I>N</I>-Sulfinylsulfonamides, <B>1a</B>, <B>b</B>, reacted with ketenimines, <B>2</B>, in ether to give the unstable [2+2] cycloadducts, 3-ylidene-1,2,4-thiadiazetidin-1-oxides, <B>3</B>, which were then readily hydrolyzed to the <I>N</I>,<I>N</I>′'-disubstituted amidine derivative, <B>4</B>, in good yields. The reaction of <I>N</I>-sulfinylmethanesulfonamide (<B>1b</B>) with diphenylketen-<I>N</I>-<I>p</I>-tolylimine (<B>2d</B>) at 130 °C gave the exchange product, <I>N</I>-sulfinyl-<I>p</I>-toluidine (<B>5</B>) in a 70% yield <I>via</I> the intermediate cycloadduct. In contrast to <B>2d</B>, the reaction of <I>N</I>-sulfinyl-<I>p</I>-toluenesulfonamide (<B>1a</B>) and phenylethylketen-<I>N</I>-phenylimine (<B>2f</B>), under the same conditions, led to the formation of a mixture of <I>N</I>-phenyl-<I>N</I>′-<I>p</I>-toluenesulfonyl-2-phenyl-<I>trans</I>- (<B>6a</B>) and <I>cis</I>-2-butenoamidine (<B>6b</B>) in an 81% yield.
- 公益社団法人 日本化学会の論文
著者
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Minami Toru
Department Of Applied Chemistry Kyushu Institute Of Technology
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Agawa Toshio
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Takimoto Futoshi
Department of Petroleum Chemistry, Faculty of Engineering, Osaka University
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