Synthesis, characterization, and nucleophilic substitutions of dimethyl(2-ferrocenoylethyl)sulfonium iodide

Abstract

Dimethyl(2-ferrocenoylethyl)sulfonium iodide was synthesized by reacting 1-ferrocenyl-4-thiapentan-1-one with iodomethane and characterized from spectral data and single crystal X-ray structure analysis. This compound was capable of reacting with different N-, S-, and O-nucleophiles giving the corresponding β-functionalized ferrocene-containing ketones. Furthermore, dimethyl sulfide can be displaced from the dimethyl(2-ferrocenoylethyl)sulfonium ion with cyanide or carbanions derived from 1,3-bifunctional compounds and nitropropane, leading to products with a new carbon-carbon bond. © 2013 Elsevier Ltd. All rights reserved.