Sulfenic esters, RSOR

The fairly closely related situation involving the rates, mechanism, and thermodynamics of the interconversion of sulfenate esters RSOR and the... 

Armed with so much data, and new insights, it was easy to predict that RS02 would be a hard acid, and RS would be a soft acid (the outer p electrons of sulfur take the place of the d electrons of the transition metals). Finding that RSO2F was stable, while RSO2I was almost impossible to make, and that RSSR disulfides were stable, while sulfenic esters, RSOR, were very unstable, simply confirmed the predictions. 

P-Chlorosulfides Sulfenyl chlorides (RSCl) are formed when sulfenate esters RSOR ) are treated with acetyl chloride (or other acid chlorides). The reactive species functionalize olefins in situ. 

The sulfenate esters RSOR also have a soft-hard make-up they are more reactive and less stable than disulfides RSSR in which both the acid and base moieties are soft. 

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See also in sourсe #XX -- [ ]

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