Dimethyl(2-oxo-2-ferrocenylethyl)sulfonium iodide - A useful synthetic equivalent of ferrocenoylcarbene in the synthesis of ferrocene-containing cyclopropanes

Abstract

The reaction of 1-ferrocenyl-3-thiabutan-1-one with methyl iodide in acetonitrile at room temperature gave dimethyl(2-oxo-2-ferrocenylethyl)sulfonium iodide, which was characterized by spectral data ( 1H NMR, 13C NMR, IR) and X-ray crystallographic analysis. This salt reacted with a base (sodium hydride) in acetonitrile yielding a stabilized ylide - dimethylsulfonium ferrocenoylmethylide, which was in turn, submitted to reactions with seven conjugated enones. The obtained results showed that this methodology is potentially a new and useful approach to ferrocene-containing cyclopropanes. © 2012 Elsevier Ltd. All rights reserved.