This report outlines a synthetic approach to a new hydrofluoroether (HFE), a new hydrofluorodiol, and a new hydrofluoroether alcohol. The route starts with the free radical addition of tetrafluoroethylene (TFE, CF2=CF2) to 2,2-dimethyl-1,3-dioxolane in presence of a radical initiator to give 4-tetrafluoroethyl-2,2-dimethyl-1,3-dioxolane (1), followed by its hydrolysis in an acidic environment to yield 3,3,4,4-tetrafluoro-1,2-butanediol (2) in quantitative yield. The insertion of TFE into one of the hydroxyl bonds of this diol under anionic conditions gives the final ether alcohol product 3,3,4,4-tetrafluoro-2-(1,1,2,2-tetrafluoroethyoxy)butan-1-ol (3) as shown in Scheme 1. This and related chemistry will be presented.

Preparation of new hydrofluoroethers (HFEs) by the addition of tetrafluoroethylene (TFE) to 2,2-dimethyl-1,3-dioxolane and subsequent reactions

255th National Meeting (2018)

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