Physical Properties and Stereochemistry of Sulphoxides

Physical Properties and Stereochemistry of Sulphoxides.—Resolution of sulphox-ides, sulphinates, and thiolsulphinates via 5-cyclodextrin inclusion complexes is not efficient ( 15%) with alkyl, aryl, or benzyl sulphoxides, but reaches 68% in the case of MeS(0)0Pr . Photoracemization of 1-naphthyl methyl sulphoxide in a cholesteric phase leads to less than 2% e.e. at equilibrium.  

Benzyl and 1-phenylethyl t-butyl sulphoxides have been shown, by measurement of dipole moments, to adopt the same conformation in solution (involving close approach of bulky groups) as has been established for the solid state through X-ray crystal analysis.  

Preparation of Saturated Sulphones.—Oxidation of sulphides and sulphoxides, using illustrates a standard method, though in the case of keten 

Preparations from sulphinic acids, SO2, other simple sulphur compounds, and sulphonyl halides are reported in the papers that are listed (with brief details) at the end of this section. The AlClj-catalysed rearrangement of an aryl arenesulphonate gives the corresponding diaryl sulphone.  

Additional Bibliography R. A. Hancock and S. T. Orszulik, Tetrahedron Lett., 1979,3789 [PhSOjCu + ArTKOCOCFjljl P. Messinger and H. Greve, Arch. Pharm. (iVeinheim, Ger.), 1978, 311,827, 

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