P-Toluenesulfinyl chloride

Titanium(IV) isopropoxide, 92-95, 99 Titanocene dichloride, 163, 164 p-Toluenesulfinyl chloride, 8 p-Toluenesulfinylimidazolide, 535 p-Toluencsulfonic acid, 535 p-Toluenesulfonyl azide, 535-536 p-Toluenesulfonyl chloride, 536 p-Toluenesulfonyl cyanide, 536 /7-Toluenesulfonylhydrazine, 537... 

N-Arylsulfoximines. These imines can be obtained in satisfactory yield by reaction of an arylamine with p-toluenesulfinyl chloride followed by oxidation... 

Little woik has been earned out on sulfinylation reactions on those systems having thiocarbonyl and imino moieties. However, hydrazones are converted to a-sulfmyl derivatives on reaction of their anions (prepared from LDA in THF) at -78 C with sulfinate esters, although the full utility of this reaction remains to be explored. Furthermore, in an unusual reaction, p-toluenesulfinyl chloride has been shown to effect a facile one-step dehydrogenation of the thiolactam (17 equation 7) in good yield. These reactions contrast with the oxidative removal of thiocarbonyl, hydrazonyl and similar functionalities with Se species (see Section 2.2.4.2). 

Preparative Methods obtained by reaction of (—)-menthol with p-toluenesulfinyl chloride. This esterification showed no particular stereoselectivity, giving an equal amount of the two sulfinate diastereomers. In order to avoid a chromatographic separation, it is possible to epimerize these sulfinate esters in acidic medium and displace the resulting equilibrium towards the less soluble isomer, (—)-menthyl (5)-p-toluenesulfinate, in 80% yield (eq 1). This procedure was later extended to large scale preparation. ... 

The ester can be prepared in 65% yieid by the reaction of p-toluenesulfinyl chloride and methanol in ether-pyridine. ... 

Sulfonyl chlorides (1, 1159). Correction The reference cited (13) refers to the preparation of p-toluenesulfinyl chloride ... 

Sulfonyl and Sulfinyl Chlorides from Sulfonic and Sulfinic Acids. Alkyl or arylsulfonyl chlorides are prepared by heating the acid with thionyl chloride DMF catalyzes this reaction. (+)-Camphorsulfonyl chloride is produced in 99% yield without a catalyst. Use of the salts of sulfinic acids minimizes their oxidation p-toluenesulfinyl chloride is produced in about 70% yield from sodium p-toluenesulfinate dihydrate with excess thionyl chloride. Phosphorus(V) Chloride is more commonly used for this transformation. 

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