The Abnormal Hydrolysis Of 7-Phosphanorbornenium Salts

Hydrolysis of phosphonium salt is one of the most fundamental and well studied reaction of the organophosphorus chemistry. The hydrolysis of 7-phosphanorbornenium salt has been well developed. We find the abnormal hydrolysis of phosphanorbornenium salts by controlling the stability of reaction intermediates. In the presence of strong base,7-Phosphanorbornenium salt is rapidly hydrolyzed to give the expected product phosphine oxide. When a weak base is used, the sole product is the secondary phosphine oxide. These experimental findings were rationalized by DFT calculations.This abnormal hydrolysis of phosphonium salt gives a new way to synthesize the secondary phosphine oxide which is considered as a potential ligand.