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, …

Y Takikawa, Y Koyama, T Yoshida, K Makino…

Index: Takikawa, Yuji; Koyama, Yutaka; Yoshida, Takamasa; Makino, Kenshiro; Shibuya, Hiroki; Sato, Kazuto; Otsuka, Tatsuya; Shibata, Yuko; Onuma, Yuki; Aoyagi, Shigenobu; Shimada, Kazuaki; Kabuto, Chizuko Bulletin of the Chemical Society of Japan, 2006 , vol. 79, # 12 p. 1913 - 1925

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Citation Number: 7

Abstract

1, 5, 3, 7-Dithiadiazocanes, 1, 5, 3, 7-diselenadiazocanes, and 1, 5, 3, 7-ditelluradiazocanes were prepared from a primary amine, formalin, and H 2 S, 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 ...