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

**Authors:** Nataliia V Kirij, Andrey A Filatov, Yurii L Yagupolskii, Sheng Peng, Lee Sprague

PMC · DOI: 10.3762/bjoc.20.40 · Beilstein Journal of Organic Chemistry · 2024-02-27

## TL;DR

Scientists developed a new method to create a fluorinated allene from hydrofluoroolefins through a halogenation/dehydrohalogenation process.

## Contribution

A novel one-pot synthesis of a fluorinated allene and its transformations is introduced.

## Key findings

- 2-halo-1,1,1,4,4,4-hexafluorobut-2-enes were synthesized and characterized.
- A new allene, 1,1,4,4,4-pentafluorobuta-1,2-diene, was successfully prepared in a one-pot reaction.
- Chemical shifts of the compounds were measured using 1H, 19F, and 13C NMR.

## 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.

## Full-text entities

- **Chemicals:** allene (MESH:C025947), 13C (MESH:C000615229), 1,1,1,4,4,4-Hexafluorobut-2-enes (-)

## Full text

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## Figures

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## References

31 references — full list in the complete paper: https://tomesphere.com/paper/PMC10910381/full.md

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Source: https://tomesphere.com/paper/PMC10910381