Novel substituent orientation in Reimer-Tiemann reactions of pyrrole-2-carboxylates

…, OM Minnetian, H Hope, MD Yanuck

Index: Smith, Kevin M.; Bobe, Frank W.; Minnetian, Ohannes M.; Hope, Hakon; Yanuck, Michael D. Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 790 - 792

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Citation Number: 17

Abstract

Reimer-Tiemann formylation reactions (base/CHClJ 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, aa 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 ...