Tetrahedron Letters p. 4195 - 4198 (1982)
Update date:2022-08-03
Topics:
Fraser, Robert R.
Baignee, Alison
Bresse, Monique
Hata, Kazumi
The changes in 13C chemical shifts for the structural change R2NH -> R2N-Li have been measured for a series of dialkylamines.These lithiation shifts are largest at the alpha carbon (3.7-9.7 ppm) and decrease in the order α > β > χ > δ.The rates of lithium-hydrogen interchange between R2NH and R'2N-Li have been determined.The activation energies are large (9 - 17 kcal/mole) and increase as the size of R or R' increases.The slow exchange permits the direct measurement of acidity differences between pairs of amines using 13C nmr.
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