Beilstein J. Org. Chem.2018,14, 106–113, doi:10.3762/bjoc.14.6
an enantiopure isotopomer of benzyl fluoride to identify whether the reaction conditions favour a dissociative (SN1) or associative (SN2) pathway. [2H]-Isotopomer ratios in the reactions were assayed using the Courtieu 2H NMR method in a chiralliquidcrystal (poly-γ-benzyl-L-glutamate) matrix and
demonstrated that both associative and dissociative pathways operate to varying degrees, according to the nature of the nucleophile and the hydrogen bond donor.
Keywords: benzylic fluorides; C–F activation; chiralliquidcrystal; 2H NMR; PBLG; stereochemistry; Introduction
The C–F bond is the strongest
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Graphical Abstract
Figure 1:
C–F activation of benzylic fluorides to generate benzylamine or diarylmethane products.