Beilstein J. Org. Chem.2024,20, 452–459, doi:10.3762/bjoc.20.40
.20.40 Abstract A series of 2,3-dihalo-1,1,1,4,4,4-hexafluorobutanes and 2-halo-1,1,1,4,4,4-hexafluorobut-2-enes were prepared from commercially available hydrofluoroolefins 1,1,1,4,4,4-hexafluorobut-2-enes and their 1H, 19F and 13C chemical shifts measured. Some reactions of synthesized 2-halo
-1,1,1,4,4,4-hexafluorobut-2-enes have been investigated. A simple, one-pot procedure for the preparation of a new allene (1,1,4,4,4-pentafluorobuta-1,2-diene) and some of its transformations is presented.
Keywords: allenes; dehydrohalogenation; halogenation; 1,1,1,4,4,4-hexafluorobut-2-enes; isomerization
all cases, except the reaction in diglyme (Table 1, entry 5), a mixture of (E)- and (Z)-2-bromo-1,1,1,4,4,4-hexafluorobut-2-enes (3a,b) in a ratio of 2:1 was formed. The configuration of the isomers was determined by the 5JFFcis coupling constant in the 19F{H} NMR spectrum (ca. 0 Hz for (Z)-isomer and
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Graphical Abstract
Scheme 1:
Synthesis of 2,3-dibromo-1,1,1,4,4,4-hexafluorobutane (2).