Summary Trimethyl (1-pyrrolyl) ammonium iodide (5 a) and the corresponding p- toluenesulfonate 5b are transformed by strong bases into 1-[(dimethylamino) methyl]-pyrrole (9), ie into a N-Mannich base, a type of compound novel in the pyrrole series. In this reaction, which is very fast in DMSO, the cation of compounds 5 is deprotonated to form the nitrogen ylide 6. The latter undergoes a Stevens-type rearrangement to 9. Several facts, ...
