Elimination versus displacement reactions: An alternative mechanistic interpretation of ‘the anomalous reactions of f-propene dimers with thiolate ions’

Abstract

In 1979 Ishikawa and Maruta reported experimental studies of the reaction of two F -propene dimers, the F -2- and 4-methyl-2-pentenes with thiolate ions. Highly unexpected products, the mercapto derivatives of F -4-methyl-1,3-pentadiene, were isolated. These authors proposed a novel mechanism which included the unprecedented 1,4-elimination of a sulfenyl fluoride from a fluorinated thioether. In the current paper the energetics of this reaction are explicitly discussed and an alternative, more precedented, mechanism is offerred.