2- Octyl p-toluenesulfonate

Nucleophilic substitution reactions of the direct displacement type proceed with inversion of configuration at the carbon atom bearing the leaving group. Thus, cis-4-t-butylcyclohexyl p-toluenesulfonate is attacked by thiophenoxide ion to give trans-4-f-butylcyclohexyl phenyl thioether. The stereoisomeric trans-p-toluenesulfonate gives the c -phenyl thioether. In the optically active 2-octyl system, enantiomeric 2-octyl p-toluenesulfonates also react with inversion of configuration when attacked by acetate ion and afford enantiomeric acetates (entry 4). 

Preparation by reaction of n-octyl p-toluenesulfonate with 2,4-dihydroxy-benzophenone,... 

Potassium cyanide has been caused to react with salts and esters of sulfonic acids to give nitriles. Thus, an intimate mixture of finely powdered potassium cyanide with the compound may be fused 422 this method was successfully applied428 to tetrahydrofurfuryl p-toluenesul-fonate and methanesulfonate, but failed with l,2 3,4-di-0-isopropylidene-6-O-tosyl-D-galactose. Another method, consisting of treatment of the ester with a stirred, boiling, saturated, aqueous solution of potassium cyanide gave885 a 70 to 83% yield of nitrile with primary p-toluenesul-fonates (ethyl, n-butyl, and n-octyl) and a 43% yield with a secondary p-toluenesulfonate (isopropyl). Similar methods had been applied earlier98 841 to such simple esters, but have not apparently found use with sulfonic esters of carbohydrates. 

Fatty acid diethanolamides, N,N-bis(2-hydroxyethyl)-N-4-octyl-N-methyl-ammonium-p-toluenesulfonate... 

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