Small electronic effects were discernible for rates of thermal racemization of various S-o-anisyl S-phenyl N-(substituted)sulfilimines. The rate was retarded by the electron-withdrawing group on the nitrogen atom. A correlation was found further between the rate and the streching frequency ( νS-N).
The Pummerer reaction of aryl prop-2-ynyl sulfoxides with acetic anhydride was found to be stereospecific. From the 18O-tracer studies, the asymmetric induction at α-carbon is considered to be caused by an intramolecular and somewhat synchronized 1,2-acetoxy migration within the ylide intermediate.
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