Synthesis of stable arsonium and sulfur ylides from perfluoroalkanesulfonyl diazocarbonyl compounds and their X-ray diffraction analysis

A series of stable fluorine-containing arsonium ylides and sulfur ylides were simply synthesized from perfluoroalkanesulfonyl diazocarbonyl compounds in the presence of rhodium catalyst. The ylide products are fairly stable due to the strong electron-withdrawing properties of perfluoroalkanesulfonyl group and carbonyl group. They are fully confirmed by spectral methods and the structures of 3ba and 3cd are also established by X-ray single crystal diffraction analysis. Several interesting features about the ylide structures and some weak fluorine interaction between them are described here.

Graphical abstractA series of stable fluorine-containing arsonium ylides and sulfur ylides were simply synthesized from perfluoroalkanesulfonyl diazocarbonyl compounds in the presence of rhodium catalyst. The ylide products are fairly stable due to the strong electron-withdrawing properties of perfluoroalkanesulfonyl group and carbonyl group. They are fully confirmed by spectral methods and the structures of 3ba and 3cd are also established by X-ray single crystal diffraction analysis. Several interesting features about the ylide structures and some weak fluorine interaction between them are described here.Figure optionsDownload full-size imageDownload as PowerPoint slide