A novel example of vinylic SRN1: Reactions of 3,3-difluoro-1-iodo-2-phenylcyclopropene with thiolate ions

The reactions of 3,3-difluoro-1-iodo-2-phenylcyclopropene with thiolate ions (with a molar ratio of 1:1) were carried out in laboratory illumination to give the corresponding substituted product. The presence of p-dinitrobenzene (p-DNB) or hydroquinone (HQ) as well as darkness significantly suppressed the reaction. ESR trapping experiments also evidenced the existence of fluorinated radical. All these results demonstrate the reaction involved a vinylic saturated alkyl and aromatic halides (SRN1) mechanism.

The reactions of 3,3-difluoro-1-iodo-2-phenylcyclopropene with thiolate ions (with a molar ratio of 1:1) are demonstrated involving a vinylic SRN1 mechanism by inhibition experiments and ESR spectrum.Figure optionsDownload as PowerPoint slide