Synthesis of Arylethylenesulfonamides and Intramolecular Rearrangement of <I>N</I>-(Arylethylenesulfonyl)thioureas
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概要
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The reactions of <I>p</I>- and <I>p</I>′- substituted <I>N</I>-(2,2-diarylethylenesulfonyl)- (<B>8</B>), <I>N</I>-[2-phenyl-2-(α-naphthyl)ethylenesulfonyl]- (<B>9</B>), and <I>N</I>-(<I>p</I>-nitrostyrene-1-sulfonyty)-<I>N</I>′-alkylthioureas (<B>12</B>) with bases afforded new intramolecularly rearranged <I>N</I>-alkyl-<I>S</I>-(2,2-diarylvinyl)- (<B>13</B>), <I>N</I>-alkyl-<I>S</I>-[2-phenyl-2-(α-naphthyl)vinyl]- (<B>14</B>), and <I>N</I>-alkyl-<I>S</I>-(<I>p</I>-nitrostyryl)isothioureas (<B>15</B>), respectively, <I>p</I>- and <I>p</I>′-Substituted 2,2-diarylethylene-<I>N</I>-methylsulfonamides (<B>6</B>) were treated with carbon disulfide and alkyl halides in the presence of a base to give alkyl 2,2-diarylvinyl trithiocarbonates (<B>17</B>). The order of reactivity of the sulfonylthioureas and -amides indicates that the rearrangement is retarded by electron-releasing <I>p</I>-substituents on benzene rings (Cl>H>CH<SUB>3</SUB>>OCH<SUB>3</SUB>).
- 公益社団法人 日本化学会の論文
著者
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Hasegawa Kiyoshi
Department Of Applied Chemistry Faculty Of Engineering Toyama University
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Hirooka Syuzi
Department Of Applied Chemistry. Faculty Of Engineering Toyama University
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Sasaki Tadashi
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
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