A NEW METHOD FOR OXIDATION OF PRIMARY AMINES TO KETONES

A series of new selective reagents has been developed for the conversion of primary amines to ketones under mild conditions. These reagents combine with the amine, R2CHNH2, to form a Schiff base, R2CHN=C<, which is rapidly transformed by prototropic rearrangement to an isomeric Schiff base. The latter base affords the desired ketone by hydrolysis in weakly acidic solution. 3,5-Di-t-butyl-l,2-benzoquinone (5), mesitylglyoxal (8a), and the nitro mesitylglyoxal derivatives 8b and 8c are shown to be highly effective reagents. With the advent of these reagents the biologically important “transamination” reaction becomes an efficient and generally useful synthetic tool. © 1969, American Chemical Society. All rights reserved.