MESO AND RACEMIC 1,1-BIS (BENZYLSULFINYL)-2-ETHYLBUTANE. A b-DISULFOXIDE PRO-LIGAND WITH STERIC RESTRICTIONS

M ZÁRRAGA O, Y MORENO N, C FRANCO O
2016 Journal of the Chilean Chemical Society (Print)  
Coordination chemistry of disulfoxides is of interest in inorganic chemistry given the well-known metal coordination through oxygen or sulfur atoms. 1 Ethylene and propylene bridged disulfoxide pro-ligands, coordinate to metals, forming coordinated and chelated complexes, demonstrating its flexibility in the formation of such complexes. 2 Some of these compounds have demonstrated interesting properties in medicinal chemistry 3 and asymmetric catalysis 4 and their synthesis is of importance for
more » ... ioorganic studies. The presence of two stereogenic centers allows the existence of the meso and racemic forms in disulfoxides. Previous studies on b-disulfoxides 5 in our laboratories have led to the synthesis and spectroscopic study ( 1 H-NMR, FT-IR) of both diastereomeric forms. In this work we report the synthesis and structural analysis of meso-(2)-and racemic-(3)-1,1-bis(benzylsulfinyl)-2-ethylbutane (Scheme1), with high steric requirement around both sulfinyl groups when a branched aliphatic carbon chain is introduced in the a-carbon. An increase in selectivity for small radius metal ions was achieved by compression of the pro-ligand coordination radius. These kind of compounds have not been previously studied. EXPERIMENTAL 1 H and 13 C NMR spectra were recorded on a Bruker AC 250 spectrometer (250 MHz for 1 H and 62.4 MHz for 13 C) in CDCl 3 and TMS as internal standard. Chemical shifts are expressed in delta units (ppm) and coupling constants in Hertz (Hz). FT-IR spectra were recorded on a Nicolet 550 IR spectrometer.
doi:10.4067/s0717-97072016000400001 fatcat:fdo6phy3jfc7bfjiy2k45myzya