meso-Bis(phenylsulfinyl)methane

Abstract

The title compound, meso-C(13)H(12)O(2)S(2), is in an anti conformation, with R and S configurations around the S atoms. The two O atoms are trans to each other, and the same applies for the two benzene rings. The phenylsulfinyl groups are nearly orthogonal to the central dithiomethane group, and the orientation of the two phenyl rings are determined by the interactions in which they are involved. The packing is built from molecular columns stabilized by weak C-H...O interactions.

Bis(phenylsulfinyl)methane

“…The relative orientations of the sulfinyl groups are virtually identical as seen in the O1-S1-S2-O2 and O3-S3-S4-O4 torsion angles of -123.31 (8) and -125.32 (8) °, respectively. These are quite distinct from the equivalent value of -178.0 (1) ° found in the meso stereo-isomer (Kannan et al, 2003). Otherwise, the equivalent bond distances in the three molecules show no special trends.…”

Different coordination modes for disulfoxides towards diorganotin(IV) dichlorides. X-ray crystal structures of 1,2-cis-bis-(phenylsulfinyl)ethene (rac-,cis-cbpse) and adducts [{Ph2SnCl2(meso-bpse)}n] and [{n-Bu2SnCl2(pdtd)}2]

“…This observation was also previously reported for other phenylsulfinyl derivative. 18 observed for our dimeric adduct, probably due to the more acidic nature of Ph 2 SnCl 2 compared to n-Bu 2 SnCl 2 , whereas the two S=O distances of 1.533(4) and 1.450(6) Å are significantly different, as a consequence of the former being complexed to tin(IV) and the latter remaining uncoordinated. However, in our dimeric adduct the shorter S=O distances of 1.501(3) and 1.512(3) Å indicate that the acid-base interactions are not strong enough.…”

“…The structure of this dissulfoxide shows that the S=O sulfinyl groups are trans to each other, and the same is observed for the Ph groups, as seen from the O1-S1-C7-C7#1 and C1-S1-C7-C7#1 torsion angles of 133.7(2)° and -117.3(2)°, respectively. The S=O groups are quasi-coplanar with the their bonded Ph rings, as shown by the O1-S1-C2-C6 torsion angle of 7.15 (18)º, due to the conjugation between the sulfur lone pairs and the π-systems of the Ph rings. This observation was also previously reported for other phenylsulfinyl derivative.…”

Nickel-Catalyzed Oxidative Coupling Reaction of Phenyl Benzyl Sulfoxides

“…Sulfoxides are generally prepared by selective oxidation of sulfides, − nucleophilic displacements on R′S­(O)­XR (XR = NR 2 or OR) with Grignard or organolithium complexes, cross-coupling with α-halo sulfoxides or direct C–H functionalization, and arylation of sulfenate anions [RS–O] − using transition metal catalysts. − Bis­(phenylsulfinyl) methanes are typically accessed by either selective oxidation of bis­(phenylsulfides) ,− or nucleophilic substitution of sulfonate esters. , In some cases, the oxidative approach leads to low yields …”

“…52,55 In some cases, the oxidative approach leads to low yields. 53 Oxidative cross-coupling methods have recently undergone rapid development, owing to their potential for green and economic synthesis. This area of intense research activity includes classical couplings, C−H functionalizations, 56 and radical chemistry for chemical, materials, and biological synthesis.…”