Abstract
AbstractThe Lewis acidity of various silyl triflates was quantified by utilizing [D5]pyridine as a 2H NMR spectroscopy probe. The chemical shifts of the 2H NMR signals for pyridine–silyl adducts are reported. The rate constants of silyl triflate catalyzed Diels–Alder reactions were determined by using UV/Vis spectroscopy. A correlation of the magnitude of the 2H NMR chemical shifts with the rate constants for most silyl triflates investigated was observed, but Me3SiOTf exhibits a surprisingly large deviation. Control experiments indicate that proton catalysis of the Diels–Alder reaction can be excluded.
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