Facile one-pot synthesis of functionalized organophosphonate esters via ketone insertion into bulky arylphosphites (original) (raw)

The reaction of phosphorus trichloride with 2,6-diisopropyl phenol in the presence of LiCl under reflux conditions for 24 h produces a mixture of (ArO)PCl 2 and (ArO) 2 PCl (Ar = 2,6-iPr 2 C 6 H 3). The hydrolysis of the aryloxy compounds in acetone/H 2 O results in the formation of two novel phosphonate ester derivatives [(ArO)P(O)(OH)(CMe 2 OH)] (1) and [(ArO) 2 P(O)(CMe 2 OH)] (2), respectively in a moderate yield. The title compounds have presumably formed via acetone insertion to the P-H bonds of (ArO)P(O)(H)(OH) and (ArO) 2 P(O)(H), respectively, in the presence of HCl produced during the hydrolysis. Compounds 1 and 2 have been characterized by elemental analysis, and ESI-mass, Infrared and NMR spectroscopic techniques. Further, solid state structures of 1 and 2 have been established by single crystals X-ray diffraction studies.