Novel Substituent Orientation in Reimer-Tiemann Reactions of Pyrrole-2-carboxylates
Reimer-Tiemann formylation reactions (base/CHCl3) on 5-substituted pyrrole-2-carboxylates (1, 6, 8, 9, 11, and 13) afford 2-formylpyrroles (5, 7, 10, 12, and 14) in which the formyl group is situated in the position originally occupied by the carboxylate function, and not, as had been expected, in the 5-unsubstituted site. These observations are confirmed by X-ray crystal structures of compounds 5, 7, and 10 and by nuclear Overhauser enhancement experiments for pyrroles 7, 10, and 14. © 1985, American Chemical Society. All rights reserved.
Publication Source (Journal or Book title)
Journal of Organic Chemistry
Smith, K., Bobe, F., Minnetian, O., Hope, H., & Yanuck, M. (1985). Novel Substituent Orientation in Reimer-Tiemann Reactions of Pyrrole-2-carboxylates. Journal of Organic Chemistry, 50 (6), 790-792. https://doi.org/10.1021/jo00206a012