A convenient and practical method for the selective preparation of deuterofluorocarbons

A detailed study of the development of efficient and practical conditions for the selective synthesis of 1-deuterononafluorobutane from 1-iodononafluorobutane is reported. The optimal conditions involve treatment of the iodo-precursor in D2O at ∼170 °C in the presence of metallic zinc in a sealed Schlenk tube to give a 59% yield of 1-deutero-1,1,2,2,3,3,4,4,4-nonafluorobutane. The same method was applied successfully to two higher homologues to produce 1-deutero-1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane and 1-deutero-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane in yields of 64% and 56%, respectively. Surprisingly, even the non-perfluorinated product 6-deutero-1,1,1,2,2,3,3,4,4-nonafluorohexane could be synthesized in 69% yield with this method.

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