Journal of Fluorine Chemistry p. 47 - 56 (1984)
Update date:2022-08-11
Topics:
Chambers, Richard D.
Jones, Colin G. P.
Silvester, Michael J.
Speight, David B.
Base-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 (68percent) and hydration gives CF3CH2COCF3 (91percent).
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