Mechanism for reaction of p-nitrotoluene with sodium polysulfide to form p-aminobenzaldehyde.
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The conversion of <I>p</I>-nitrotoluene to <I>p</I>-aminobenzaldehyde was found to be most effectively done by a mixture of Na<SUB>2</SUB>S<SUB>4</SUB> and <I>ca.</I> two equivalents of NaOH to <I>p</I>-nitrotoluene. After examination of probable intermediates, toluidine, <I>p</I>-nitrobenzaldehyde and <I>p</I>-nitrosotoluene were discarded as the intermediate. The reaction of carbanion ArCO\={C}HAr with the sulith the sulfide and the effect of some nitrobenzenes as an electron accepter were examined. These results suggest a mechanism involving a simultaneous oxidation-reduction in a nitrotoluene molecule.
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