Tris(2-perfluorhexylethyl)methan jako nový synthon ve fluorové chemii

David KŘEPELKA

Bachelor's thesis

Tris(2-perfluorohexylethyl)methane as a new synthon in fluorous chemistry

Abstract:

Dehydratací alkoholu 1 tris(2-perfluorhexylethyl)methanol byl připraven alken 2 1,1-bis(2-perfluorhexylethyl)-3-perfluorhexylpropen. Z alkenu 2 byl hydrogenací připraven alkan 3 1,1-bis(2-perfluorhexylethyl)-3-perfluorhexylpropenunatris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridekafluoroktyl)methan. Na základě nespolehlivosti hydrogenace pro přípravu alkanu 3 přistoupeno k alternativní metodě hydroborací a acidobazickým rozkladem na alkan 3. Dále provedeny modelové reakce s terc-BuLi a ketony 6 butanon a 9 2,3,4,5 tetramethyl cyclopent 2 enon. Následně proveden pokus přípravy organolitného činidla 11 tris(2-perfluorhexylethyl)methanlithium.

Abstract:

We have prepared alken 2 1,1-bis(2-perfluorhexylethyl)-3-perfluorhexylpropene by dehydratation of alkohol 1 tris(2-perfluorhexylethyl)methanol. Then we have prepared alkan 3 1,1-bis(2-perfluorhexylethyl)-3-perfluorhexylpropenunatris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridekafluoroktyl)methane by hydrogenation of alken 2. Because hydrogenation was unreliable for preparation of alkan 3 we have decided to use alternative approach in preparation. Alternative method was hydroboration of alken 2 followed by quenching which was suppose to result into alkan 3. We have also performed model reaction of terc-BuLi with keton 6 butanon and 9 2,3,4,5 tetramethyl cyclopent 2 enon with following preparation of organolithium reagent 11 tris(2-perfluorhexylethyl)methanlithium.

Keywords

Fluorová chemie, perfluorovaná sloučenina, dehydratace, hydrogenace, hydroborace, organolitné činidlo.

Language used: Czech

Date on which the thesis was submitted / produced: 14. 8. 2020

Accessible from:: 31. 12. 2999

Thesis defence

• Supervisor: doc. Ing. Jan Čermák, CSc.

JAN EVANGELISTA PURKYNĚ UNIVERSITY IN ÚSTÍ NAD LABEM

Faculty of Science

Bachelor programme / field:
Chemistry / Toxicology and Hazardous Waste Analysis