Chlorination and mesylation at the hydroxymethyl position of deuterium-labeled N -substituted 2-(hydroxymethyl)pyrroles has been shown to occur with some involvement of a highly reactive azafulvenium species. An electron-withdrawing camphorsulfonyl substituent on nitrogen provides a chiral handle for direct analysis of the stereochemical outcome of the reactions by 1 H NMR.
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Abell et al. (1999) studied this question.
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