Abstract
The cathodic behavior of 2-pheny1-4,4-dimethyl-2-oxazoline (4), 2,4,4-trimethyl-2-oxazoline (7) and 2-(1,1-dimethylethyl)-4,4-dimethyl-2-oxazoline (8) at Hg electrodes was investigated. A reduction peak for 4 at -2.49V(SCE), was observed by cyclic voltammetry (CV). Preparative reduction of 4 at a mercury pool yielded exclusively N-benzyl-2-amino-2-methylpropanol (6) in a high yield (91%). The electrolysis procedure was simple utilizing constant current and an undivided cell, and the pH remained neutral throughout the reaction. The 2-oxazolines 7 and 8 did not exhibit CV reduction peaks and were recovered after attempts of preparative electrolysis. CV and nmr measurements indicate that the reduction of 4 involves initial formation of the corresponding oxazolidine 5 followed by ring cleavage to the easily reducible tautomeric imine 5a which reacts to give 6.
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