Electrophilic substitution in pyrroles. Part 4. Hydrogen exchange in acid solution

Abstract
Hydrogen exchange at the unsubstituted positions in 1,2,5-trimethyl- and 1,3,4-trimethyl-pyrrole in aqueous buffer has been examined. The two positions were found to be of similar reactivities. General acid catalysis was detected. No hydrogen exchange on the methyl groups of 2,3,4,5-tetramethylpyrrole, even in strong acid, was detected. The 13C n.m.r. spectrum of the tetramethylpyrrole was examined.

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