Stereochemistry of nucleophilic additions to hexafluoro-2-butyne
Review articleOpen access

AbstractBase-catalysed additions of alcohols to F-2-butyne (1) give mainly products of trans-addition while cis-addition predominates in uncatalysed additions of alcohols carried out in a diluent. The stereochemistry of addition of diethylamine is very dependent on the solvent used and cis- or trans-addition may predominate. Stepwise and concerted mechanisms are advanced to account for these observations. Nucleophilic addition of sulphur to (1) gives F-tetramethylthiophene (68%) and hydration gives CF3CH2COCF3 (91%).

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