ESR 1: Etienne Lisse - August to September 2016

Title: Screening of SNAr-VNS reactions on fluorinated dicarbonyl systems

Host University: Institute of Organic Chemistry and Biochemistry

Accommodation: Lodging House of the IOCB, Prague 6, Czech Republic

Science: Investigating the possibility of applying fluorinated dicarbonyl systems to SNAr or Vicarious Nucleophilic Substitutions (VNS), different synthetic conditions have been tested (NaH, K2CO3, LiHMDS, nBuLi, LDA, tBuOK, or phase transfer catalytic processes based on cinchonidinium salts catalysts) with either 2-fluoro-1,3-dimethylmalonate or 2-fluoroethylacetoacetate (previously synthesized in Durham University) using different conditions, temperatures and solvents and involving 5-fluoro-3-nitro-1-pentafluorosulfanylbenzene, whose synthesis has been optimized using F2/N2 in UOCHB Prague.

New Skills acquired

Interpersonal Skills

  • Ability to work in a new environment for a very short period of time
  • Efficient management of time and space
  • Improvement of my team-working skills
  • Ability to efficiently communicate and present results in front of early-stage researchers

Scientific skills

  • Use of a computer-assisted fluorination line
  • Purification by computer-assisted automatic column chromatography
  • Improvement of my 19F-NMR spectroscopy skills dealing with synthesized molecules containing SF5 functional group
  • Improvement of my GC-MS command