Synthesis of a new carbbenzyloxymethylenetriparatolylphosphorane ylide and study of its reaction with mercury(II) halides: Spectral and structural characterization

A new carbbenzyloxymethylenetriparatolylphosphorane ylide (BTPY), {(p-tolyl)3PCHCOOCH2C6H5},was synthesized and characterized with elemental analysis as well as various spectroscopic techniques. The reactions of the title ylide with mercury(II) chloride, mercury(II) bromide and mercury(II) iodide in equimolar ratios using dry methanol as solvent have yielded [BTPY · HgCl2]2 (1), [BTPY · HgBr2]2 (2) and [BTPY · HgI2]2 (3), respectively. Single crystal X-ray analysis of 2 reveals the presence of a centrosymmeteric dimeric structure containing the ylide and HgBr2. The analytical data, IR and 1H, 13C and 31P NMR data for the latter compound are similar to those of 1 and 3, indicating similar structures. The theoretical studies indicated that, for all three compounds, the observed trans-like structure for compound 2, is more stable than the possible cis-like structure in each case.

Graphical abstractThe reaction of a new phosphorus ylide, carbbenzyloxymethylenetriparatolylphosphorane, {(p-tolyl)3PCHCOOCH2C6H5}, with a mercury(II) halide yields a dimeric complex of the form [{(p-tolyl)3PCHCOOCH2C6H5}(HgX2)]2 ( where X = Cl, Br or I). Single crystal X-ray analyses of 2 reveals the presence of centrosymmeteric dimeric structure containing the ylide and HgBr2.Figure optionsDownload full-size imageDownload as PowerPoint slide