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
作者:Yuji Takikawa、Yutaka Koyama、Takamasa Yoshida、Kenshiro Makino、Hiroki Shibuya、Kazuto Sato、Tatsuya Otsuka、Yuko Shibata、Yuki Onuma、Shigenobu Aoyagi、Kazuaki Shimada、Chizuko Kabuto
DOI:10.1246/bcsj.79.1913
日期:2006.12
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
分别从
伯胺、
福尔马林和 H 2 S、NaSeH 或 NaTeH 制备 1,5,3,7-二
硫重氮烷、1,5,3,7-二
硒重氮烷和 1,5,3,7-二
碲重氮烷. 使用
NBS 氧化 1,5,3,7-二
硒二氮杂环烷和 1,5,3,7-二
碲二氮杂环烷分别有效地提供 1,2,4-二
硒唑烷或 1,2,4-二
碲唑烷。相比之下,用
溴元素
硫或
二氯化二硫 (S 2 Cl 2 ) 处理 1,5,3,7-二
噻唑并得到 1,2,3,4,5,7-五
噻唑烷。假设 1,5,3,7-二
硫代二氮杂环烷类化合物通过原位形成 1,5,3,7-二
硫代二
氮杂双环 [3.3.0]
辛烷型二氮杂环进行不寻常的氧化转化。