Preparation of sydnone compounds substituted by thio and seleno functional groups at the 4-positions.

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概要

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• The introduction of thio and seleno functional groups to the 4-position of a sydnone ring was successfully attempted using 4-lithiosydnones (<B>2</B>) and 4-bromosydnones (<B>3</B>) as starting compounds. The reaction of <B>2</B> with tetraalkylthiuram disulfides, bis[alkoxy(thiocarbonyl)] disulfides, and bis[alkylthio(thiocarbonyl)] disulfides provided 4-sydnonyl dithiocarbamates, <I>O</I>-alkyl <I>S</I>-(4-sydnonyl) dithiocarbonates, and dialkyl 4-sydnonyl trithiocarbonates, respectively in good yields. In addition, treatment of <B>2</B> with thiocyanogen and selenocyanogen gave rise to bis(4-sydnonyl) sulfides (<B>11</B>) and bis(4-sydnonyl) selenides (<B>12</B>), respectively. These products, <B>11</B> and <B>12</B> were also formed by the reaction of <B>3</B> with potassium thiocyanate and selenocyanate, respectively. Furthermore, it was found that <B>3</B> reacted with selenourea and potassium <I>O</I>-ethyl dithiocarbonate under heating to provide <B>12</B> and <B>11</B>, respectively. It was also found that the reactivity of these sydnone compounds <B>2</B> and <B>3</B> was quite different in many cases from that of the corresponding ordinary aromatic analogues, though the sydnone ring has a somewhat aromatic nature.

• 公益社団法人 日本化学会の論文

著者

• Nonaka Tsutomu

  Department Of Electric Chemistry Tokyo Institute Of Technology

• Tien Hsien-ju

  Department Of Chemistry National Cheng Kung University

• Fuchigami Toshio

  Department Of Electronic Chemistry Tokyo Institute Of Technology

• Chen Ching-Sy

  Department of Electronic Chemistry, Graduate School at Nagatsuta, Tokyo Institute of Technology

• Yen Mou-Yung

  Department of Chemistry, National Cheng Kung University

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