Helvetica Chimica Acta

1??[(Dimethylamino) methyl] pyrrol aus Trimethyl (1??pyrrolyl)??ammonium??Ion

P Zeltner, K Bernauer

Index: Zeltner, Peter; Bernauer, Karl Helvetica Chimica Acta, 1983 , vol. 66, # 6 p. 1860 - 1864

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Citation Number: 4

Abstract

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, ...