(4) We find that both indole and N-ethylindole undergo deuterium exchange at the 3-position (nmr) with DOAc at 20'to the extent of-40 and-50%(mass spectrometry), respectively, after 2 hr.(5) JA Marshall and WS Johnson, J. Org. Chem., 28, 421 (1963); see also C. Djerassi, HJ Monteiro, A. Walser, and LJ Durham, J. Amer. Chem. SOC., 88, 1792 (1966).
[Chiappe, Cinzia; De Rubertis, Antonietta; Detert, Heiner; Lenoir, Dieter; Wannere, Chaitanya S.; Schleyer, Paul Von R. Chemistry - A European Journal, 2002 , vol. 8, # 4 p. 967 - 978]