NMR Studies of Complexes of Fluorides of Triethylamine

Abstract

Different mole ratio of triethylamine HF (Et 3 .nHF, n= 3, 4 and 5) adducts were prepared and 1 H and

In Situ Generated DBU⋅HF Acts as a Fluorinating Agent in a Hexafluoroisobutylation Tandem Reaction: An Effective Route to 5,5,5,5’,5’,5’‐Hexafluoroleucine

“…The formation of compound 2 was successfully observed and 3 was gradually consumed until full conversion. Surprisingly, the 19 F NMR signal from DBU⋅HF was not observed in [D 8 ]THF, possibly due to hydrogen bond exchange with THF broadening the peak (Figure S2) [26] . These NMR experiments confirm that the reaction proceeds through a tandem allylic shift/hydrofluorination process and shows that only 1 equiv.…”

“…Surprisingly, the 19 F NMR signal from DBU•HF was not observed in [D 8 ]THF, possibly due to hydrogen bond exchange with THF broadening the peak (Figure S2). [26] These NMR experiments confirm that the reaction proceeds through a tandem allylic shift/hydrofluorination process and shows that only 1 equiv. of the fluoride is necessary to drive the reaction to completion.…”