Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Preparation of Sydnone Compounds Substituted by Thio and Seleno Functional Groups at the 4-Positions
Toshio FuchigamiChing-Sy ChenTsutomu NonakaMou-Yung YenHsien-Ju Tien
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1986 Volume 59 Issue 2 Pages 487-491


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

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