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Preparation of (perfluoroalkyl)alkane thiols via Zemplén deacylation of fluorous (perfluoroalkyl)alkyl thioacetates

[Display omitted] •Adaption of Zemplén deacylation for thioacetates.•Effective stochiometric synthesis of thioacetates from iodides and/or sulfonates.•Pure perfluoroalkyl thioacetates and thiols are accessible without chromatography. Convenient and robust synthesis of (perfluoroalkyl)alkane thiols [...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2018-06, Vol.210, p.70-77
Main Authors: Menczinger, Bálint, Nemes, Anikó, Szíjjártó, Csongor, Rábai, József
Format: Article
Language:English
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Summary:[Display omitted] •Adaption of Zemplén deacylation for thioacetates.•Effective stochiometric synthesis of thioacetates from iodides and/or sulfonates.•Pure perfluoroalkyl thioacetates and thiols are accessible without chromatography. Convenient and robust synthesis of (perfluoroalkyl)alkane thiols [(CnF2n+1(CH2)mSH); m/n = 3/4,6,8,10, 4a-d; m/n = 2/6, 8; m/n = 1/1,2,3,7,8H, 12a-e] was developed starting from commercially available fluorous alcohols (1a-d, 5, 9a-e). The intermediate (perfluoroalkyl)alkyl iodides and/or sulfonates were reacted with potassium thioacetate in DMF, and the resulting thioacetates were deacetylated by a Zemplén analogue reaction. The (perfluoroalkyl)alkane thiols were obtained in good overall yields and high purity.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2018.02.014