Abstract
1‐[(Dimethylamino)methyl]pyrrole from Trimethyl (1‐pyrrolyl)ammonium IonTrimethyl (1‐pyrrolyl)ammonium iodide (5a) and the corresponding p‐toluene‐sulfonate 5b are transformed by strong bases into 1‐[(dimethylamino)methyl]‐pyrrole (9), i.e. 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, namely the negative outcome of a cross‐reaction experiment with 3,4‐dimethylpyrrole and of an attempt to obtain 9 from pyrrole and dimethyl (methylidene)ammonium iodide in the presence of one equivalent of sodium methoxide, as well as unsuccessful CIDNP studies point to a rearrangement mechanism via the contact ion pair 12.
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