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Preparation of (perfluoroalkyl)alkane thiols via Zemplén deacylation of fluorous (perfluoroalkyl)alkyl thioacetates
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2018-03-03 , DOI: 10.1016/j.jfluchem.2018.02.014
Bálint Menczinger , Anikó Nemes , Csongor Szíjjártó , József Rábai

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.



中文翻译:

氟(全氟烷基)烷基硫代乙酸酯的Zemplén脱酰反应制备(全氟烷基)烷硫醇

(全氟烷基)烷硫醇[(C n F 2n + 1(CH 2m SH); / Ñ  = 3 / 4,6,8,10,4A - d ; m / n  = 2/ 6,8 ; M / N  = 1 / 1,2,3,7,8H,12A - ë ]被开发由市售氟醇(起始1A - d5图9a - ë)。使中间体(全氟烷基)烷基碘化物和/或磺酸盐与硫代乙酸钾在DMF中反应,然后通过Zemplén类似反应使所得的硫代乙酸酯脱乙酰。以良好的总收率和高纯度获得了(全氟烷基)链烷硫醇。

更新日期:2018-03-03
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