One step synthesis of 1,1,1,4,4,4-hexafluorobutane from succinonitrile

Bromine trifluroide (BrF 3) reacts with succinonitrile (NCCH 2CH 2CN) to form 1,1,1,4,4,4-hexafluorobutane as the major product. A minor amount of bromo-1,1,1,4,4,4-hexafluorobutane (∼5% of total trapped products) was also formed. BrF 3 reacts with succinonitrile to form these hexafluorobutanes at a...

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Bibliographic Details
Published in:Journal of fluorine chemistry 1999-04, Vol.94 (2), p.123-126
Main Authors: Baker, Max T, Ruzicka, Jan A, Tinker, John H
Format: Article
Language:English
Subjects:
1,1,1,4,4,4-hexafluorobutane
Bromine trifluoride
Bromo-1,1,1,4,4,4-hexafluorobutane
Fluorination
HFC-356mff
Succinonitrile
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Description
Summary:Bromine trifluroide (BrF 3) reacts with succinonitrile (NCCH 2CH 2CN) to form 1,1,1,4,4,4-hexafluorobutane as the major product. A minor amount of bromo-1,1,1,4,4,4-hexafluorobutane (∼5% of total trapped products) was also formed. BrF 3 reacts with succinonitrile to form these hexafluorobutanes at ambient temperature or higher, in the absence of a moderating solvent, and in the absence of a catalyst. These results demonstrate that BrF 3 directly converts nitriles to trifluoromethyl moieties and is useful in the synthesis of bis-trifluoromethyl containing compounds.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(98)00311-X