Radical Addition of Bis(Trimethylsilyl)Phosphonate to Vinyltrimethylsilane: Crystal Structure of (2-Trimethylsilylethyl)Phosphonic Acid

Abstract

The formation of phosphorus-carbon bond by free radical addition of phosphorus compounds containing P-H bond to olefins has been known since more than three decades ago. Alkyl or aryl phosphins, phosphinates, phosphonates and phosphorus or hypophosphorus acid have been used in these reactions, but a little attention have been paid to silyl phosphonates. As a part of ongoing study on the structure and reactivity of organosilicon-phosphonate compounds, we synthesized bis(trimethylsi1yl) (2-trimethylsilylethyl)phosphonate (I) by the reaction of bis(trimethylsily1) phosphonate with vinyltrimethylsilane in the presence of a peroxide. The product was characterized by its ¹H and ³¹P NMR and IR spectra. Hydrolysis of (I) led to the formation of corresponding phosphonic acid (n). The crystal structure of (11) has been determined by X-ray diffraction analysis.