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Toshio Fuchigami, Ching-Sy Chen, Tsutomu Nonaka, Mou-Yung Yen, Hsien-Ju Tien, Preparation of Sydnone Compounds Substituted by Thio and Seleno Functional Groups at the 4-Positions, Bulletin of the Chemical Society of Japan, Volume 59, Issue 2, February 1986, Pages 487–491, https://doi.org/10.1246/bcsj.59.487
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Abstract
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.
