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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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Published in: | Journal of fluorine chemistry 2018-06, Vol.210, p.70-77 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0022-1139 1873-3328 |
DOI: | 10.1016/j.jfluchem.2018.02.014 |