97771-67-0Relevant articles and documents
Synthesis and oxidative ring contraction of 1,5,3,7-dichalcogenadiazocanes. Novel formation of 1,2,4-diselenazolidines, 1,2,4-ditellurazolidines, and 1,2,3,4,5,7-pentathiazocanes
Takikawa, Yuji,Koyama, Yutaka,Yoshida, Takamasa,Makino, Kenshiro,Shibuya, Hiroki,Sato, Kazuto,Otsuka, Tatsuya,Shibata, Yuko,Onuma, Yuki,Aoyagi, Shigenobu,Shimada, Kazuaki,Kabuto, Chizuko
, p. 1913 - 1925 (2006)
1,5,3,7-Dithiadiazocanes, 1,5,3,7-diselenadiazocanes, and 1,5,3,7-ditelluradiazocanes were prepared from a primary amine, formalin, and H2S, NaSeH, or NaTeH, respectively. Oxidation of 1,5,3,7- diselenadiazocanes and 1,5,3,7-ditelluradiazocanes using NBS efficiently afforded 1,2,4-diselenazolidines or 1,2,4-ditellurazolidines, respectively. In contrast, treatment of 1,5,3,7-dithiadiazocanes with bromine-elemental sulfur or disulfur dichloride (S2Cl2) afforded 1,2,3,4,5,7- pentathiazocanes. An unusual oxidative conversion of 1,5,3,7- dichalcogenadiazocanes into these products was assumed to proceed through in situ formation of 1,5,3,7-dichalcogenadiazabicyclo[3.3.0]octane-type dications.