Abstract
Reaction of the N-oxide of R2BuN (R = Me or Bu) with iron(II) ion gives the hydroxy-derivatives R2N·[CH2]2·CH(OH)Me and R2N·[CH2]3·CH2·OH, as well as the parent amine and a secondary amine. Evidence is presented that the hydroxy-compounds are formed from the amine radical cation R2BuN+˙via intramolecular hydrogen-atom transfer which occurs specifically at the terminal carbon of the butyl group; the resulting carbon radical yields the primary alcohol by way of one-electron oxidation, and the secondary alcohol partly by way of one-electron oxidation and intramolecular rearrangement and partly via intermolecular hydrogen-atom abstraction.
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