Journal of the American Chemical Society

Organosulfur chemistry. Part 55. Fluorodestannylation. A powerful technique to liberate anions of oxygen, sulfur, selenium, and carbon

DN Harpp, M Gingras

Index: Harpp, David N.; Gingras, Marc Journal of the American Chemical Society, 1988 , vol. 110, # 23 p. 7737 - 7745

Full Text: HTML

Citation Number: 77

Abstract

Abstract: Fluoride ions smoothly destannylate organotin chalcogenides to liberate nucleophilic chalcogenide ions; hence the first nucleophilic oxide (02-) and selenide (Se2-) transfer agents are reported where the tin atom serves as a “group 16 (VIB) transfer agent”. In the presence of crown ethers or ammonium salts, this process results in a new way to generate “naked” nucleophiles. Ethers and selenides are formed in good to excellent yield ...

~69%

~88%

~19%

~52%

~92%

~96%

~77%

First example of selenium transfer reaction of primary selen...

[Ming-De, Ruan; Hua-Rong, Zhao; Wei-Qiang, Fan; Xun-Jun, Zhou Journal of Organometallic Chemistry, 1995 , vol. 485, # 1-2 p. 19 - 24]

Conditions-driven selective synthesis of selenides and selen...

[Krief, Alain; Trabelsi, Mahmoud; Dumont, Willy; Derock, Michel Synlett, 2004 , # 10 p. 1751 - 1754]

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]

Synthesis of diselenides and selenides from elemental seleni...

[Krief, Alain; Derock, Michel Tetrahedron Letters, 2002 , vol. 43, # 16 p. 3083 - 3086]

Flash pyrolysis of selenides. Syntheses of bibenzyls, olefin...

[Higuchi, Hiroyuki; Otsubo, Tetsuo; Ogura, Fumio; Yamaguchi, Hachiro; Sakata, Yoshiteru; Misumi, Soichi Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 1 p. 182 - 187]