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

Bálint Menczinger, Anikó Nemes, Csongor Szíjjártó, J. Rábai

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Abstract

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.

Original languageEnglish
Pages (from-to)70-77
Number of pages8
JournalJournal of Fluorine Chemistry
Volume210
DOIs
Publication statusPublished - Jun 1 2018

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Keywords

  • Fluorous
  • Nonaflates
  • Perfluoroalkyl
  • Thiols
  • Triflates

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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