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Hydrogen Abstraction from Amines: Formation of Aminyl vs. α-Aminoalkyl Radicals
Nazran, A. S.,Griller, D.
, p. 1970 - 1971 (2007/10/02)
A series of electron paramagnetic experiments were carried out which showed that dialkylaminyl radicals do not readily attack dialkylamines to form α-aminoalkyl radicals.These results disprove earlier conclusions that such processes were the major pathways for formation of α-aminoalkyl radicals in free radical reactions involving dialkylamines.By contrast, tert-butoxyl radicals were found to efficiently abstract hydrogen from amines.Rate constants for C-H and N-H abstraction by tert-butoxyl were respectively 6.5 x 107 and 1.1 x 107 for Me2NH, 6.6 x 107 and 1.0 x 107 for Et2NH, 1.3 x 107 and 3 x 106 for n-PrNH2, 7 x 106 and 3 x 106 for n-BuNH2, and 3.3 x 106 for t-BuNH2 (units M-1 s-1).
