69978-09-2Relevant academic research and scientific papers
Synthesis of Sydnone Compounds Substituted by Heteroatom Groups at the 4-Positions
Fuchigami, Toshio,Chen, Ching-Sy,Nonaka, Tsutomu,Yeh, Mou-Yung,Tien, Hsien-Ju
, p. 483 - 486 (2007/10/02)
A general method for the introduction of heteroatoms to the 4-position of a sydnone ring was developed.Various 4-alkylthio- and 4-arylthiosydnones were prepared in excellent yields by the reaction of 3-aryl-4-lithiosydnones (2) with dialkyl and diaryl disulfides.Treatment of 2 with diaryl diselenides, diphenylphosphinous chloride, and arsenic trichloride provided 3-aryl-4-(arylseleno)sydnones, (3-aryl-4-sydnonyl)diphenylphosphine and tris(3-aryl-4-sydnonyl)arsine, respectively, in good yields.It was also found that the reactivity of sydnonyl anions derived from 2 was quite different in some cases from that of the corresponding ordinary aromatic analogues, though the sydnone ring has a somewhat aromatic nature.
