Highly efficient route to diselenides from the reactions of imines and selenium in the presence of carbon monoxide and water
…, J Chen, X Wu, S Wu, WJ Xiao, Z Zheng
Index: Zhao, Xiaodan; Yu, Zhengkun; Zeng, Fanlong; Chen, Jinzhu; Wu, Xiaowei; Wu, Sizhong; Xiao, Wen-Jing; Zheng, Zhaoyan Advanced Synthesis and Catalysis, 2005 , vol. 347, # 6 p. 877 - 882
Full Text: HTML
Citation Number: 7
Abstract
Abstract Reactions of selenium with imines (RR 1 C [DOUBLE BOND] NR 2) of aldehydes and ketones in the presence of carbon monoxide, water and triethylamine lead to reductive selenation, on aerobic work-up, to afford symmetrical diselenides (RR 1 CHSe) 2 in good to excellent yields. The proposed mechanism suggests that both in situ generated carbonyl selenide (SeCO) and hydrogen selenide (H 2 Se) are involved in the reaction.
Related Articles:
A novel synthesis of organic diselenides
[Huang, Zhi-Zhen; Liu, Fei-Yan; Du, Jing-Xing; Huang, Xian Organic Preparations and Procedures International, 1995 , vol. 27, # 4 p. 492 - 494]
[Wang, Jin-Xian; Bai, Lin; Li, Wenbo; Hu, Yulai Synthetic Communications, 2000 , vol. 30, # 2 p. 325 - 332]
[Shimada, Kazuaki; Jin, Norikazu; Kawaguchi, Michiko; Dobashi, Kumiko; Nagano, Yumi; Fujimura, Manabu; Kudoh, Eiichi; Kai, Tomonari; Saito, Noboru; Masuda, Jun-Ichi; Iwaya, Masaki; Fujisawa, Hiroyuki; Aoyagi, Shigenobu; Takikawa, Yuji Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 1 p. 197 - 206]
[Takikawa, Yuji; Uwano, Akira; Watanabe, Hiroyuki; Asanuma, Masaki; Shimada, Kazuaki Tetrahedron Letters, 1989 , vol. 30, # 44 p. 6047 - 6050]
[Gladysz,J.A. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 1204 - 1208]