(E, Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

Nataliia V Kirij; Andrey A Filatov; Yurii L Yagupolskii; Sheng Peng; Lee Sprague

doi:10.3762/bjoc.20.40

(E, Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

Beilstein J Org Chem. 2024 Feb 27:20:452-459. doi: 10.3762/bjoc.20.40. eCollection 2024.

Authors

Nataliia V Kirij¹, Andrey A Filatov¹, Yurii L Yagupolskii¹, Sheng Peng², Lee Sprague²

Affiliations

¹ Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar Str., 5, Kyiv-94, 02660, Ukraine.
² The Chemours Company, Chemours Discovery Hub, Newark, DE 19713, United States.

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: 1,1,1,4,4,4-hexafluorobut-2-enes; allenes; dehydrohalogenation; halogenation; isomerization.